CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 1988, Vol. 60, No. 1, pp. 39-48

http://dx.doi.org/10.1351/pac198860010039

Metal-directed stereoselective functionalization of alkenes in organic synthesis

W. Oppolzer

CrossRef Cited-by theme picture

CrossRef Cited-by Linking

  • Piątek Anna, Chapuis Christian: Influence of norbornanone substituents on both the Wagner–Meerwein skeletal rearrangements under sulfonation conditions and the diastereoselectivity of the corresponding N,N′-bis-fumaroyl sultams in uncatalyzed Diels–Alder cycloadditions to cyclopenta-1,3-diene. Tetrahedron Letters 2013, 54, 4247. <http://dx.doi.org/10.1016/j.tetlet.2013.05.147>
  • Piątek Anna M., Sadowska Agnieszka, Chapuis Christian, Jurczak Janusz: Diastereoselective Alkyl Grignard 1,4-Additions to para-Substituted (2R)-N-Cinnamoylbornane-10,2-sultam Derivatives: Influence of N-Atom Pyramidalization. J Helv Chim Acta 2011, 94, 2141. <http://dx.doi.org/10.1002/hlca.201100197>
  • Gmeiner Peter: An efficient and practical EPC synthesis of β-amino acids from L-asparagine. Arch Pharm Pharm Med Chem 2010, 324, 551. <http://dx.doi.org/10.1002/ardp.2503240906>
  • Bragnier Nicolas, Guillot Regis, Scherrmann Marie-Christine: Diastereoselective addition of sugar radicals to camphorsultam glyoxilic oxime ether: a route toward C-glycosylthreonine and allothreonine. Org Biomol Chem 2009, 7, 3918. <http://dx.doi.org/10.1039/b910050d>
  • El-Batta Amer, Bergdahl Mikael: Copper(I) iodide dimethyl sulfide catalyzed 1,4-addition of alkenyl groups from alkenyl-alkylzincate reagents. Tetrahetron Lett 2007, 48, 1761. <http://dx.doi.org/10.1016/j.tetlet.2007.01.041>
  • Voigt Katharina, Lansky Annegret, de Meijere Armin, Noltemeyer Mathias: The Use of Vicinal Twofold Heck Reaction Products in Diastereoselective Sequential Michael Additions - A Convenient Access to Enantiomerically Pure Six-Ring Anellated Cispentacin Derivatives. Liebigs Ann /Recueil 2006, 1996, 899. <http://dx.doi.org/10.1002/jlac.199619960607>
  • Lelais Gérald, Seebach Dieter: β2-amino acids—syntheses, occurrence in natural products, and components of β-peptides1,2. Biopolymers (Biospectroscopy) 2004, 76, 206. <http://dx.doi.org/10.1002/bip.20088>
  • Mamaghani Manouchehr, Tabatabaeian Khalil, Badrian Abed: SYNTHESIS OF THE CHIRAL α,β-UNSATURATED N-ACYL-OXAZOLIDIN-2-ONES BY WITTIG REACTION. Phosphorus Sulfur Silicon Relat Elem 2004, 179, 1347. <http://dx.doi.org/10.1080/10426500490468155>
  • Spino Claude: CHIRAL ENOLATE EQUIVALENTS. A REVIEW. Org Prep Proced Int 2003, 35, 1. <http://dx.doi.org/10.1080/00304940309355794>
  • Voges R.: From chiral bromo[13,14Cn]acetyl sultams to complex molecules singly/multiply labelled with isotopic carbon. J Labelled Cpd Radiopharm 2002, 45, 867. <http://dx.doi.org/10.1002/jlcr.610>
  • Jolivet Catherine, Long Daniel D., Dahl Russel S., Termin Andreas P.: Structural elucidation and complete assignment of a novel class of sulfonamides: bridgehead tricyclic sultams. Magn Reson Chem 2002, 40, 307. <http://dx.doi.org/10.1002/mrc.1006>
  • Long Daniel D, Dahl Russell, Jolivet Catherine, Marshall Will J, Termin Andreas P: Stereo- and regiospecific formation of a highly functionalized bridgehead tricyclic sultam. Tetrahetron Lett 2002, 43, 4407. <http://dx.doi.org/10.1016/S0040-4039(02)00560-9>
  • Hatano Manabu, Terada Masahiro, Mikami Koichi: Highly Enantioselective Palladium-Catalyzed Ene-Type Cyclization of a 1,6-Enyne. Angew Chem 2001, 113, 255. <http://dx.doi.org/10.1002/1521-3757(20010105)113:1<255::AID-ANGE255>3.0.CO;2-R>
  • Hatano Manabu, Terada Masahiro, Mikami Koichi: Highly Enantioselective Palladium-Catalyzed Ene-Type Cyclization of a 1,6-Enyne. Angewandte Chemie-Int Ed 2001, 40, 249. <http://dx.doi.org/10.1002/1521-3773(20010105)40:1<249::AID-ANIE249>3.0.CO;2-X>
  • Michelet Véronique, Galland Jean-Christophe, Charruault Lise, Savignac Monique, Genêt Jean-Pierre: Efficient Metallo−Ene Reactions in Organoaqueous Phase. Org Lett 2001, 3, 2065. <http://dx.doi.org/10.1021/ol016023f>
  • Muchow Gunter, Brunel Jean Michel, Maffei Michel, Pardigon Olivier, Buono Gérard: Pd(0) catalyzed asymmetric amination of a prochiral bicyclic allylic diacetate. Tetrahedron 1998, 54, 10435. <http://dx.doi.org/10.1016/S0040-4020(98)00496-7>
  • Bauer Tomasz: Syntheses of deoxyhexoses from diastereoisomerically pure hetero-Diels-Alder adduct. Tetrahedron 1997, 53, 4763. <http://dx.doi.org/10.1016/S0040-4020(97)00159-2>
  • Brzezinski Linda Joy, Rafel Sara, Leahy James W.: The asymmetric Baylis-Hillman reaction as a template in organic synthesis. Tetrahedron 1997, 53, 16423. <http://dx.doi.org/10.1016/S0040-4020(97)01025-9>
  • Heumann Andreas, Réglier Marius: The stereochemistry of palladium catalysed cyclisation reactions part C: Cascade reactions. Tetrahedron 1996, 52, 9289. <http://dx.doi.org/10.1016/0040-4020(96)00545-5>
  • Miyake Tsutomu, Seki Masahiko, Nakamura Yoshinori, Ohmizu Hiroshi: Synthesis of a novel chiral 1, 3-benzoxazinone auxiliary and its application to highly diastereoselective aldol reaction. Tetrahetron Lett 1996, 37, 3129. <http://dx.doi.org/10.1016/0040-4039(96)00508-4>
  • Tanaka Kiyoshi, Ahn Mija, Watanabe Yukari, Fuji Kaoru: Asymmetric synthesis of uncommon α-amino acids by diastereoselective alkylations of a chiral glycine equivalent. Tet Asymm 1996, 7, 1771. <http://dx.doi.org/10.1016/0957-4166(96)00212-1>
  • Dodin-carnot V., Stephan B., Curci M., Mieloszynski J. L., Paquer D.: ACTION OF DITHIOPHOSPHORIC ACID TOWARDS SULFURATED ALKYNES IN PRESENCE OF TRANSITION-METAL-CATALYST. Phosphorus Sulfur Silicon Relat Elem 1996, 108, 1. <http://dx.doi.org/10.1080/10426509608029631>
  • Heumann Andreas, Réglier Marius: The stereochemistry of palladium-catalysed cyclisation reactions part B: Addition to π-allyl intermediates. Tetrahedron 1995, 51, 975. <http://dx.doi.org/10.1016/0040-4020(94)01011-N>
  • Sibi Mukund P., Deshpande Prasad K., Ji Jianguo: A new chiral oxazolidinone derived from diphenylalaninol. Aldol, alkylation, and diels-alder reactions. Tetrahetron Lett 1995, 36, 8965. <http://dx.doi.org/10.1016/0040-4039(95)01984-P>
  • Martín Nazario, Martínez-Grau Angeles, Seoane Carlos, Marco JoséL.: Stereocontrolled routes to derivatives of 3-alkoxycarbonyl-2-amino-4-aryl-5-cyano-6-phenyl-4H-pyrans. Tet Asymm 1995, 6, 255. <http://dx.doi.org/10.1016/0957-4166(94)00382-L>
  • Davies Stephen G., Sanganee Hitesh J.: 4-Substituted-5,5-dimethyl oxazolidin-2-ones as effective chiral auxiliaries for enolate alkylations and Michael additions. Tet Asymm 1995, 6, 671. <http://dx.doi.org/10.1016/0957-4166(95)00057-V>
  • Starý Ivo, Stará Irena G., Kocˇovský Pavel: Palladium(O)-catalyzed allylic substitution with allylic alkoxides as substrates. Tetrahedron 1994, 50, 529. <http://dx.doi.org/10.1016/S0040-4020(01)80774-2>
  • Amputch Mary A., Matamoros Regina, Little R.Daniel: Asymmetric induction in the Michael Initiated Ring Closure reaction. Tetrahedron 1994, 50, 5591. <http://dx.doi.org/10.1016/S0040-4020(01)85631-3>
  • Drewes Siegfried E., Malissar Dean G. S., Roos Gregory H. P.: Ephedrine-Derived Imidazolidin-2-ones. Broad Utility Chiral Auxiliaries in Asymmetric Synthesis. Chem Ber 1993, 126, 2663. <http://dx.doi.org/10.1002/cber.19931261216>
  • Touriya Zair, Christiane Santelli-Rouvier, Maurice Santelli: Palladium-mediated cyclization of 1,5-hexadien-3-ols to 1-methyl-1,3-cyclopentadienes. Tetrahedron 1993, 49, 3313. <http://dx.doi.org/10.1016/S0040-4020(01)90160-7>
  • Oppolzer Wolfgang, Lienard Phillippe: Non-destructive Cleavage ofN-Acylsultams Under Neutral Conditions: Preparation of Enantiomerically, Pure Fmoc-Protected α-Amino Acids. HCA 1992, 75, 2572. <http://dx.doi.org/10.1002/hlca.19920750812>
  • Starý Ivo, Zajíček Jaroslav, Kočovský Pavel: Stereochemistry of the palladium-catalyzed allylic substitution: the syn-anti dichotomy in the formation of (π-allyl)palladium complexes and their equilibration. Tetrahedron 1992, 48, 7229. <http://dx.doi.org/10.1016/S0040-4020(01)88263-6>
  • Ager David J., East Michael B.: Methodology to establish 1,2- and 1,3-difunctionality for the synthesis of carbohydrate derivates. Tetrahedron 1992, 48, 2803. <http://dx.doi.org/10.1016/S0040-4020(01)90970-6>
  • Gmeiner Peter: Efficient EPC synthesis of β-aminobutanoic acid. Liebigs Ann Chem 1991, 1991, 501. <http://dx.doi.org/10.1002/jlac.199119910190>
  • Zair Touriya, Santelli-Rouvier Christiane, Santelli Maurice: Palladium-mediated cyclization of 1,5-hexadien-3-ols to 1-methyl-1,3-cyclopentadienes. Tetrahetron Lett 1991, 32, 4501. <http://dx.doi.org/10.1016/0040-4039(91)80023-Y>
  • Engelbrech G.J., Holzapfel C.W.: Stereoselective palladium catalyzed cyclization on carbohydrate templates- a route to chiral cyclopentanes and some heterocyclic analogs. Tetrahetron Lett 1991, 32, 2161. <http://dx.doi.org/10.1016/S0040-4039(00)71264-0>
  • Seebach Dieter: Organische Synthese — wohin?. Angew Chem 1990, 102, 1363. <http://dx.doi.org/10.1002/ange.19901021118>
  • Hegedus Louis S.: Transition metals in organic synthesis annual survey covering the year 1988. J Organomet Chem 1990, 380, 169. <http://dx.doi.org/10.1016/0022-328X(90)80270-A>
  • Oppolzer Wolfgang, Tamura Osamu: Asymmetric synthesis of α-amino acids and α-N-hydroxyamino acids via electrophilic amination of bornanesultam-derived enolates with 1-chloro-1-nitrosocyclohexane. Tetrahetron Lett 1990, 31, 991. <http://dx.doi.org/10.1016/S0040-4039(00)94411-3>
  • Wills Martin, Starkemann Christian, Oppolzer Wolfgang, Bernardinelli Gérald: Chiral toluene-2,α-sultam auxiliaries: Preparation and structure of enantiomerically pure (2R)- and (S)-ethyl-2,1′-sultam. Tetrahetron Lett 1990, 31, 4117. <http://dx.doi.org/10.1016/S0040-4039(00)97557-9>
  • Oppolzer Wolfgang, Wills Martin, Kelly Martha J., Signer Marcel, Blagg Julian: Chiral toluene-2,α-sultam auxiliaries: Asymmetric diels-alder reactions of N-enoyl derivatives. Tetrahetron Lett 1990, 31, 5015. <http://dx.doi.org/10.1016/S0040-4039(00)97793-1>
  • Gmeiner Peter: General synthesis of enantiomerically pure β-amino acids. Tetrahetron Lett 1990, 31, 5717. <http://dx.doi.org/10.1016/S0040-4039(00)97940-1>
  • Oppolzer Wolfgang: Intramolekulare stöchiometrische (Li, Mg, Zn) und katalytische (Ni, Pd, Pt) Metallo-En-Reaktionen in der Organischen Synthese. Angew Chem 1989, 101, 39. <http://dx.doi.org/10.1002/ange.19891010106>
  • Oppolzer Wolfgang: Intramolecular, Stoichiometric (Li, Mg, Zn) and Catalytic (Ni, Pd, Pt) Metallo-Ene Reactions in Organic Synthesis [New Synthetic Methods (75)]. Angew Chem Int Ed Engl 1989, 28, 38. <http://dx.doi.org/10.1002/anie.198900381>
  • Oppolzer Wolfgang, Swenson Rolf E., Pachinger Werner: Palladium(0)-Catalyzed Cyclizations of Simple 1-Aryl-1,7-octadien-3-yl Acetates. Preliminary communication. HCA 1989, 72, 14. <http://dx.doi.org/10.1002/hlca.19890720103>
  • Oppolzer Wolfgang, Rodriguez Inès, Blagg Julian, Bernardinelli Gérald: AsymmetricDiels-Alder reactions: X-Ray crystal-structure analysis of [N-((E)-But-2-enoyl)bornane-10,2-sultam]tetrachlorotitanium. HCA 1989, 72, 123. <http://dx.doi.org/10.1002/hlca.19890720116>
  • Oppolzer Wolfgang, Kingma Arend J.: Asymmetric Induction on Copper(I) Chloride catalyzed 1,4-addition of alkylmagnesium chlorides to α, β-disubstituted (E)-enoylsultams and subsequent protonation. HCA 1989, 72, 1337. <http://dx.doi.org/10.1002/hlca.19890720622>
  • Binger Paul, Brinkmann Axel, Roefke Petra, Schäfer Bernd: Reaktionen der Methylencyclopropane, XI Asymmetrische Nickel(0)-katalysierte [3 + 2]-Cycloadditionen von Methylencyclopropanen mit chiralen Acrylsäure-Derivaten. Liebigs Ann Chem 1989, 1989, 739. <http://dx.doi.org/10.1002/jlac.198919890222>
  • Oppolzer Wolfgang, Kingma Arend J., Poli Giovanni: Asymmetric 1,4-additions of gilman reagents to α,β - disubstitoted (e)-enoylsultams / “enolate” protonations. Tetrahedron 1989, 45, 479. <http://dx.doi.org/10.1016/0040-4020(89)80075-4>
  • Oppolzer Wolfgang, Keller Thomas H., Bedoya-Zurita Manuel, Stone Charles: Diastereocontrolled nickel(0)- and palladium(0) catalyzed “metallo-ene-type” cyclizations/carbonylations. Tetrahetron Lett 1989, 30, 5883. <http://dx.doi.org/10.1016/S0040-4039(01)93496-3>
  • Oppolzer Wolfgang, Moretti Robert, Thomi Silvia: Asymmetric alkylation of N-acylsultams: A general route to enantiomerically pure, crystalline C(α,α)-disubstituted carboxylic acid derivatives. Tetrahetron Lett 1989, 30, 5603. <http://dx.doi.org/10.1016/S0040-4039(01)93810-9>
  • Oppolzer Wolfgang, Moretti Robert, Thomi Silvia: Asymmetric alkylations of a sultam-derived glycinate equivalent: practical preparation of enantiomerically pure α-amino acids. Tetrahetron Lett 1989, 30, 6009. <http://dx.doi.org/10.1016/S0040-4039(01)93840-7>
  • Yamamoto Keiji, Terakado Masahiko, Murai Kouya, Miyazawa Masahiro, Tsuji Jiro, Takahashi Kazuhiko, Mikami Koichi: Palladium (0)-catalyzed cyclization-carbonylation of 2,7-octadienyl acetate and analogs. Chem Lett 1989, 955. <http://dx.doi.org/10.1246/cl.1989.955>
  • Oppolzer Wolfgang, Gaudin Jean-Marc, Birkinshaw Timothy N.: Palladium-catalyzed intramolecular olefin allylations: Stereocontrolled syntheses of bicyclic systems and evidence for an allylpalladium/olefin-cis-insertion. Tetrahetron Lett 1988, 29, 4705. <http://dx.doi.org/10.1016/S0040-4039(00)80586-9>
  • Oppolzer W., Gaudin J.-M., Bedoya-Zurita M., Hueso-Rodriguez J., Raynham T.M., Robyr C.: Synthesis of nitrogen- or oxygen- containing ring systems by palladium-catalyzed intramolecular olefin allylations. Tetrahetron Lett 1988, 29, 4709. <http://dx.doi.org/10.1016/S0040-4039(00)80587-0>
  • Oppolzer Wolfgang, Swenson Rolf E., Gaudin Jean-Marc: Catalytic intramolecular 2-(4-alkenyl)allylpalladium insertions. Tetrahetron Lett 1988, 29, 5529. <http://dx.doi.org/10.1016/S0040-4039(00)80804-7>
  • Oppolzer Wolfgang, Radinov Rumen N.: Enantioselective synthesis of sec-allylalcohols by catalytic asymmetric addition of divinylzinc to aldehydes. Tetrahetron Lett 1988, 29, 5645. <http://dx.doi.org/10.1016/S0040-4039(00)80834-5>
  • Oppolzer Wolfgang, Dupuis Dominique, Poli Giovanni, Raynham Tony M., Bernardinelli Gérald: Enantioselective synthesis and absolute configuration of (−)-pulo'upone by asymmetric intramolecular diels-alder reaction. Tetrahetron Lett 1988, 29, 5885. <http://dx.doi.org/10.1016/S0040-4039(00)82216-9>
  • Oppolzer Wolfgang, Bedoya-Zurita Manuel, Switzer Christopher Y.: Nickel-catalyzed intramolecular allylation of alkenes and alkynes coupled with β-elimination or carbonylation. Tetrahetron Lett 1988, 29, 6433. <http://dx.doi.org/10.1016/S0040-4039(00)82365-5>