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Pure Appl. Chem., 1988, Vol. 60, No. 1, pp. 57-64

http://dx.doi.org/10.1351/pac198860010057

Organocuprate addition to α,β-unsaturated compounds: synthetic and mechanistic aspects

C. Ullenius and B. Christenson

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  • Bloom Steven, Sharber Seth Andrew, Holl Maxwell Gargiulo, Knippel James Levi, Lectka Thomas: Metal-Catalyzed Benzylic Fluorination as a Synthetic Equivalent to 1,4-Conjugate Addition of Fluoride. J. Org. Chem. 2013, 78, 11082. <http://dx.doi.org/10.1021/jo401796g>
  • Yoshikai Naohiko, Nakamura Eiichi: Mechanisms of Nucleophilic Organocopper(I) Reactions. Chemistry Review 2012, 112, 2339. <http://dx.doi.org/10.1021/cr200241f>
  • Hogan Philip J., Powell Lyn, Robinson Graham E.: Development of a Catalytic Cuprate 1,6-Conjugate Dienone Addition Process for the Manufacture of Fulvestrant EAS, a Key Intermediate in the Synthesis of Fulvestrant. Org Process Res Dev 2010, 14, 1188. <http://dx.doi.org/10.1021/op1001319>
  • Shi Min, Zhang Wen: Asymmetric 1,4-Addition of Diethylzinc to Cyclic Enones Catalyzed by Cu(I)-Chiral Sulfonamide-Thiophosphoramide Ligands and Lithium Salts. Adv Synth Catal 2005, 347, 535. <http://dx.doi.org/10.1002/adsc.200404321>
  • Pfretzschner Tatjana, Kleemann Lutz, Janza Birgit, Harms Klaus, Schrader Thomas: On the Role of PIII Ligands in the Conjugate Addition of Diorganozinc Derivatives to Enones. Chem Eur J 2004, 10, 6048. <http://dx.doi.org/10.1002/chem.200400316>
  • Asao Naoki, Lee Sunyoung, Yamamoto Yoshinori: π–π Chelation controlled chemoselective conjugate addition of lithium dimethylcuprate. Tetrahetron Lett 2003, 44, 1803. <http://dx.doi.org/10.1016/S0040-4039(03)00095-9>
  • Gustafsson Björn, Håkansson Mikael, Westman Gunnar, Jagner Susan: A tetrameric copper(I) alkoxide with a π-tethered ligand: 2-allyl-6-methylphenoxocopper(I). J Organomet Chem 2002, 649, 204. <http://dx.doi.org/10.1016/S0022-328X(02)01126-9>
  • Bertozzi Fabio, Crotti Paolo, Macchia Franco, Pineschi Mauro, Feringa Ben L.: Highly Enantioselective Regiodivergent and Catalytic Parallel Kinetic Resolution. Angew Chem 2001, 113, 956. <http://dx.doi.org/10.1002/1521-3757(20010302)113:5<956::AID-ANGE956>3.0.CO;2-T>
  • Karlström A. Sofia E., Bäckvall Jan-E.: Experimental Evidence Supporting a CuIII Intermediate in Cross-Coupling Reactions of Allylic Esters with Diallylcuprate Species. Chem Eur J 2001, 7, 1981. <http://dx.doi.org/10.1002/1521-3765(20010504)7:9<1981::AID-CHEM1981>3.0.CO;2-C>
  • Bertozzi Fabio, Crotti Paolo, Macchia Franco, Pineschi Mauro, Feringa Ben L.: Highly Enantioselective Regiodivergent and Catalytic Parallel Kinetic Resolution. Angew Chem Int Ed 2001, 40, 930. <http://dx.doi.org/10.1002/1521-3773(20010302)40:5<930::AID-ANIE930>3.0.CO;2-7>
  • Börner Christoph, König Wilfried A, Woodward Simon: Enone structure as a probe to Lewis acid carbonyl binding in copper-catalysed asymmetric conjugate addition. Tetrahetron Lett 2001, 42, 327. <http://dx.doi.org/10.1016/S0040-4039(00)01940-7>
  • Andersen Denise L., Back Thomas G.: Stereochemistry of Cuprate-Mediated Conjugate Additions of a 17-Iodoandrost-16-ene to E- and Z-6-Methylhept-2-en-4-one. Collect Czech Chem Commun 2001, 66, 1797. <http://dx.doi.org/10.1135/cccc20011797>
  • Nakamura Eiichi, Mori Seiji: Warum denn Kupfer? – Strukturen und Reaktionsmechanismen von Organocupratclustern in der Organischen Chemie. Angew Chem 2000, 112, 3902. <http://dx.doi.org/10.1002/1521-3757(20001103)112:21<3902::AID-ANGE3902>3.0.CO;2-L>
  • Nakamura Eiichi, Mori Seiji: Wherefore Art Thou Copper? Structures and Reaction Mechanisms of Organocuprate Clusters in Organic Chemistry. Angew Chem 2000, 39, 3750. <http://dx.doi.org/10.1002/1521-3773(20001103)39:21<3750::AID-ANIE3750>3.0.CO;2-L>
  • Kitamura Masato, Miki Takashi, Nakano Keiji, Noyori Ryoji: 1,4-Addition of Diorganozincs to .ALPHA.,.BETA.-Unsaturated Ketones Catalyzed by a Copper(I)-Sulfonamide Combined System. Bull Chem Soc Jpn 2000, 73, 999. <http://dx.doi.org/10.1246/bcsj.73.999>
  • Kingsbury Celia L., Sharp Kelly S., Smith Robin A.J.: Effects of dimethyl sulfide on the reaction of dibutylcopper reagents with α,β-unsaturated ketones. Tetrahedron 1999, 55, 14693. <http://dx.doi.org/10.1016/S0040-4020(99)00915-1>
  • Huang Hui, Liang Chong H., Penner-Hahn James E.: Röntgenabsorptionsspektroskopie von Dimethylcupraten: Hinweis auf eine lösungsmittelabhängige Aggregation. Angew Chem 1998, 110, 1628. <http://dx.doi.org/10.1002/(SICI)1521-3757(19980605)110:11<1628::AID-ANGE1628>3.0.CO;2-7>
  • Krause Norbert, Gerold Andreas: Regio- und stereoselektive Synthesen mit Organokupferreagentien. Angew Chem 1997, 109, 194. <http://dx.doi.org/10.1002/ange.19971090304>
  • Gerold Andreas, Jastrzebski Johann T. B. H., Kronenburg Claudia M. P., Krause Norbert, Van Koten Gerard: Bestimmung des Aggregationsgrades von Organokupfer-Verbindungen durch Kryoskopie in Tetrahydrofuran. Angew Chem 1997, 109, 778. <http://dx.doi.org/10.1002/ange.19971090720>
  • Feringa Ben L., Pineschi Mauro, Arnold Leggy A., Imbos Rosalinde, De Vries André H. M.: Hochenantioselektive katalytische 1,4-Addition und kombinierte 1,4-Addition/Aldolreaktion von Organozinkreagentien an Enone. Angew Chem 1997, 109, 2733. <http://dx.doi.org/10.1002/ange.19971092316>
  • H��ffner Fredrik, Brinck Tore, Haeberlein Markus, Moberg Christina: Force field parameterization of copper(I)-olefin systems from density functional calculations. Journal of Molecular Structure: THEOCHEM 1997, 397, 39. <http://dx.doi.org/10.1016/S0166-1280(96)04978-0>
  • Orsini Fulvia, Rinaldi Sabina: Application of (2R,3R)-dihydroxy-1,2,3,4-tetrahydronaphthalene to asymmetric synthesis. Tet Asymm 1997, 8, 1039. <http://dx.doi.org/10.1016/S0957-4166(97)00088-8>
  • de Vries AndréH.M., Imbos Rosalinde, Feringa Ben L.: (+)-Camphor-derived tri- and tetradentate amino alcohols; synthesis and application as ligands in the nickel catalyzed enantioselective conjugate addition of diethylzinc. Tet Asymm 1997, 8, 1467. <http://dx.doi.org/10.1016/S0957-4166(97)00145-6>
  • De Vries André H. M., Meetsma Auke, Feringa Ben L.: Enantioselektive, durch neuartige chirale Phosphoramidit-Kupferkomplexe katalysierte konjugierte Addition von Dialkylzink-Reagentien an cyclische und acyclische Enone. Angew Chem 1996, 108, 2526. <http://dx.doi.org/10.1002/ange.19961082020>
  • Fuji Kaoru, Yang Xiao-Shen, Tanaka Kiyoshi, Asakawa Naoyuki, Hao Xiao-Jian: 1,1′-Binaphthalene-8,8′-diol as an efficient chiral controller: Highly enantioselective synthesis of optically active ketones. Tetrahetron Lett 1996, 37, 7373. <http://dx.doi.org/10.1016/0040-4039(96)01659-0>
  • Persson Eva S. M., van Klaveren Mayra, Grove David M., Bäckvall Jan E., van Koten Gerard: ortho-Chelating Arenethiolatocopper(I) Complexes as Versatile Catalysts in the Regioselective Cross-Coupling of Allylic Derivatives withnBuMgI—An Example of Reversed Reactivity of Leaving Groups. Chem Eur J 1995, 1, 351. <http://dx.doi.org/10.1002/chem.19950010605>
  • Lang Heinrich, Köhler Katrin, Blau Sabine: η2-Alkyne copper(I) and silver(I) compounds; from polymeric [MIR]η to monomeric [MIR] units (MCu, Ag). Coord Chem Rev - 1995, 143, 113. <http://dx.doi.org/10.1016/0010-8545(94)07001-Z>
  • Cunico Robert F., Zhang Cui-ping: A conjugate addition-elimination route to alkenoyltrimethylsilanes. Tetrahedron 1995, 51, 9823. <http://dx.doi.org/10.1016/0040-4020(95)00561-L>
  • Zhu Jie, van der Hoeven John: Facial stereoselectivity in lithium dialkylcuprate additions to functionalized endo-Tricyclo[5.2.1.02,6]decadienones. Tetrahedron 1995, 51, 10953. <http://dx.doi.org/10.1016/0040-4020(95)00651-N>
  • Klaveren Mayra van, Lambert François, Eijkelkamp Desiree J.F.M., Grove David M., van Koten Gerard: Arenethiolatocopper(I) complexes as homogeneous catalysts for Michael addition reactions. Tetrahetron Lett 1994, 35, 6135. <http://dx.doi.org/10.1016/0040-4039(94)88097-2>
  • van Klaveren Mayra, Persson Eva S.M., Grove David M., Bäckvall Jan-E., van Koten Gerard: The use of ortho-chelating arenethiolate non-transferable groups in the copper(I) catalyzed selective α or γ substitution of acyclic allylic substrates with grignard reagents. Tetrahetron Lett 1994, 35, 5931. <http://dx.doi.org/10.1016/S0040-4039(00)78222-0>
  • Lipshutz Bruce H., James Brian: Effects of additives on cuprate 1,4-additions: Gilman reagents in the presence of Me3SiCN. Tetrahetron Lett 1993, 34, 6689. <http://dx.doi.org/10.1016/S0040-4039(00)61676-3>
  • Melnyk Oleg, Stephan Elie, Pourcelot Guy, Cresson Pierre: Additions diastéréosélectives d'alkyl, alcényl, aryl et allyl cuprates à des imides chirales insaturées. Tetrahedron 1992, 48, 841. <http://dx.doi.org/10.1016/S0040-4020(01)88188-6>
  • 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>
  • Yamamoto Keiko, Yamada Sachiko, Yamaguchi Kentaro: Highly diastereoselective conjugate addition of organocuprate to acyclic E- and Z-enones: Reversal Stereoselectivity under kinetic and thermodynamic conditions. Tetrahetron Lett 1992, 33, 7521. <http://dx.doi.org/10.1016/S0040-4039(00)60813-4>
  • Shanna Sunaina, Oehlschlager Allan C.: Evidence for intermediate π-complexes in the addition of trialkylsilyl and trialkylstannylcuprates to β, β-unsaturated enones. Tetrahedron 1991, 47, 1177. <http://dx.doi.org/10.1016/S0040-4020(01)86374-2>
  • Christenson Beritte, Hallnemo Gerd, Ullenius Christina: Stereoselective addition of R2CuLi to ortho-substituted methyl cinnamates intramolecular assistance and solvent effects. Tetrahedron 1991, 47, 4739. <http://dx.doi.org/10.1016/S0040-4020(01)86478-4>
  • Fang Chenglin, Ogawa Tomoyuki, Suemune Hiroshi, Sakai Kiyoshi: Asymmetric conjugate addition of organometallic reagents to chiral α, β-unsaturated esters. Tet Asymm 1991, 2, 389. <http://dx.doi.org/10.1016/S0957-4166(00)82125-4>
  • Lenders Bernd, Kläui Wolfgang: Alken-, Alkin-, Isonitril- und Carbonyl-Komplexe von Kupfer(I) und Silber(1) mit dreizähnigen Sauerstoff-Chelatliganden. Chem Ber 1990, 123, 2233. <http://dx.doi.org/10.1002/cber.19901231202>
  • 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>
  • Alexakis A., Sedrani R., Mangeney P.: Stereochemical effects of trimethylsilyl chloride (TMSCl) on the conjugate addition of organocopper reagents. Tetrahetron Lett 1990, 31, 345. <http://dx.doi.org/10.1016/S0040-4039(00)94551-9>
  • Fang Chenglin, Suemune Hiroshi, Sakai Kiyoshi: Chiral alcohol-induced diastereoselective conjugate addition and cyclization. Tetrahetron Lett 1990, 31, 4751. <http://dx.doi.org/10.1016/S0040-4039(00)97723-2>
  • Bernardi Anna, Capelli Anna M., Gennari Cesare, Scolastico Carlo: 1,4-addition to α,β-unsaturated carbonyl compounds bearing a γ-stereocenter: A molecular mechanics model for steric interactions in the transition state. Tet Asymm 1990, 1, 21. <http://dx.doi.org/10.1016/S0957-4166(00)82267-3>
  • 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>
  • Smith Robin A.J., Vellekoop A.Samuel: An investigation of the electron transfer properties of modified organocofper reagents and higher-order cuprates. Tetrahedron 1989, 45, 517. <http://dx.doi.org/10.1016/0040-4020(89)80079-1>
  • Christenson Beritte, Olsson Thomas, Ullenius Christina: Addition of Me2CuLi to ortho-substituted methyl cinnamates an NMR study of the π-complex formation. Tetrahedron 1989, 45, 523. <http://dx.doi.org/10.1016/0040-4020(89)80080-8>
  • van Koten Gerard, Jastrzebski Johann T.B.H.: Polynuclear aryl-copper species and neutral aryl-cuprates with a chiral-CH(Me)NMe2 ortho substituent. Tetrahedron 1989, 45, 569. <http://dx.doi.org/10.1016/0040-4020(89)80084-5>
  • Alexakis A., Sedrani R., Mangeney P., Normant J.F.: Diastereoselective conjugate addition with acetals, oxazolidines and imidazolidines as chiral auxiliaries. Tetrahetron Lett 1988, 29, 4411. <http://dx.doi.org/10.1016/S0040-4039(00)80509-2>