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Pure Appl. Chem., 1998, Vol. 70, No. 8, pp. 1501-1506

http://dx.doi.org/10.1351/pac199870081501

Chiral relay auxiliaries

S. D. Bull, S. G. Davies, D. J. Fox, A. C. Garner and T. G. R. Sellers

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  • Wang Bao-Yu, Stojanović Sandra, Turner Daniel A., Young Tanya L., Hadad Christopher M., Badjić Jovica D.: The Entrapment of Chiral Guests with Gated Baskets: Can a Kinetic Discrimination of Enantiomers Be Governed through Gating?. Chem. Eur. J. 2013, 19, 4767. <http://dx.doi.org/10.1002/chem.201204344>
  • Ghosh Jyotirmoy, Sil Parames C.: Arjunolic acid: A new multifunctional therapeutic promise of alternative medicine. Biochimie 2013, 95, 1098. <http://dx.doi.org/10.1016/j.biochi.2013.01.016>
  • Baranov Denis S., Gold Brian, Vasilevsky Sergei F., Alabugin Igor V.: Divergent Cyclizations of 1-R-Ethynyl-9,10-anthraquinones: Use of Thiourea as a “S2–” Equivalent in an “Anchor-Relay” Addition Mediated by Formal C–H Activation. J. Org. Chem. 2013, 78, 2074. <http://dx.doi.org/10.1021/jo302146r>
  • Davies Stephen G., Fletcher Ai M., Thomson James E.: Direct asymmetric syntheses of chiral aldehydes and ketones via N-acyl chiral auxiliary derivatives including chiral Weinreb amide equivalents. Chem. Commun. 2013, 49, 8586. <http://dx.doi.org/10.1039/c3cc45463k>
  • Davies Stephen G., Lee James A., Roberts Paul M., Thomson James E., Yin Jingda: Double asymmetric induction as a mechanistic probe: the doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure α,β-unsaturated esters and enantiopure α,β-unsaturated hydroxamates. Tetrahedron 2011, 67, 6382. <http://dx.doi.org/10.1016/j.tet.2011.05.102>
  • Stojanović Sandra, Turner Daniel A., Hadad Christopher M., Badjić Jovica D.: Controlling dynamic stereoisomerism in transition-metal folded baskets. Chem Sci 2011, 2, 752. <http://dx.doi.org/10.1039/c0sc00592d>
  • Yamada Shinji, Fossey John S.: Nitrogen cation–π interactions in asymmetric organocatalytic synthesis. Biomol Chem 2011, 9, 7275. <http://dx.doi.org/10.1039/c1ob05228d>
  • Bull Steven D., Davies Stephen G., Fox David J., Garner A. Christopher, Sellers Thomas G. R.: ChemInform Abstract: Chiral Relay Auxiliaries. ChemInform 2010, 30, no. <http://dx.doi.org/10.1002/chin.199925266>
  • Hitchcock Shawn R., Dean Melissa A., Kelley Christopher J., Edler Kate L., Ferrence Gregory M.: Synthesis and X-ray crystal structures of chiral, nonracemic 5,6-dihydro-4H-1,3,4-oxadiazines. J Heterocyclic Chem 2010, 47, 982. <http://dx.doi.org/10.1002/jhet.402>
  • Bentley Scott A., Davies Stephen G., Lee James A., Roberts Paul M., Russell Angela J., Thomson James E., Toms Steven M.: Conjugate addition of lithium N-tert-butyldimethylsilyloxy-N-(α-methylbenzyl)amide: asymmetric synthesis of β2,2,3-trisubstituted amino acids. Tetrahedron 2010, 66, 4604. <http://dx.doi.org/10.1016/j.tet.2010.04.027>
  • De Risi Carmela, Pelà Michela, Pollini Gian Piero, Trapella Claudio, Zanirato Vinicio: Mastering chiral substituted 2-oxopiperazines. Tet Asymm 2010, 21, 255. <http://dx.doi.org/10.1016/j.tetasy.2010.02.008>
  • Duguet Nicolas, Donaldson Adele, Leckie Stuart M., Douglas James, Shapland Peter, Brown Thomas B., Churchill Gwydion, Slawin Alexandra M.Z., Smith Andrew D.: Chiral relay in NHC-mediated asymmetric β-lactam synthesis I; substituent effects in NHCs derived from (1R,2R)-cyclohexane-1,2-diamine. Tet Asymm 2010, 21, 582. <http://dx.doi.org/10.1016/j.tetasy.2010.03.001>
  • Duguet Nicolas, Donaldson Adele, Leckie Stuart M., Kallström Eddy A., Campbell Craig D., Shapland Peter, Brown Thomas B., Slawin Alexandra M.Z., Smith Andrew D.: Chiral relay in NHC-mediated asymmetric β-lactam synthesis II; asymmetry from NHCs derived from acyclic 1,2-diamines. Tet Asymm 2010, 21, 601. <http://dx.doi.org/10.1016/j.tetasy.2010.03.002>
  • Cheeseman Matt, Davies Iwan R., Axe Phil, Johnson Andrew L., Bull Steven D.: A temporary stereocentre approach for the asymmetric synthesis of chiral cyclopropane-carboxaldehydes. Org Biomol Chem 2009, 7, 3537. <http://dx.doi.org/10.1039/b908600e>
  • Axe Philip, Bull Steven D., Davidson Matthew G., Jones Matthew D., Robinson Diane E. J. E., Mitchell William L., Warren John E.: An enantiopure pseudo-C3-symmetric titanium triflate with propeller-like chirality as a catalyst for asymmetric sulfoxidation reactions. Dalton Trans 2009, 10169. <http://dx.doi.org/10.1039/b918141p>
  • Hitchcock Shawn R., Davis Ryan A., Richmond Daniel M., Dore Delvis D., Kuschel Stephanie L., Vaughn Jeremy F., Wolfe Jesse A., Hamaker Christopher G., Casper David M., Dingle Jarvis: Synthesis, asymmetric aldol reactions, and x-ray crystallography of some oxadiazinanone derivatives. J Heterocyclic Chem 2008, 45, 1265. <http://dx.doi.org/10.1002/jhet.5570450502>
  • Undheim K.: The Schöllkopf chiron and transition metal mediated reactions, a powerful combination for stereoselective construction of cyclic α-quaternary-α-amino acid derivatives. Amino Acids 2008, 34, 357. <http://dx.doi.org/10.1007/s00726-007-0512-5>
  • Parrott Raleigh W., Hitchcock Shawn R.: Intramolecular chiral relay at stereogenic nitrogen: oxazolidine catalysts derived from Ephedra alkaloids. Tet Asymm 2007, 18, 377. <http://dx.doi.org/10.1016/j.tetasy.2006.12.029>
  • Reginato Gianna, Di Credico Barbara, Andreotti Daniele, Mingardi Anna, Paio Alfredo, Donati Daniele: A new versatile and diastereoselective synthesis of polysubstituted 2-oxopiperazines from naturally occurring amino acids. Tet Asymm 2007, 18, 2680. <http://dx.doi.org/10.1016/j.tetasy.2007.10.027>
  • Hoover Trisha R., Groeper Jonathan A., Parrott Raleigh W., Chandrashekar Seshanand P., Finefield Jennifer M., Dominguez Alexandro, Hitchcock Shawn R.: Towards the development of oxadiazinanones as chiral auxiliaries: synthesis and application of N3-haloacetyloxadiazinanones. Tet Asymm 2006, 17, 1831. <http://dx.doi.org/10.1016/j.tetasy.2006.06.036>
  • Dore Delvis D., Burgeson James R., Davis Ryan A., Hitchcock Shawn R.: Synthesis, reactivity and conformational stability of an l-phenylalanine derived oxadiazinanone. Tet Asymm 2006, 17, 2386. <http://dx.doi.org/10.1016/j.tetasy.2006.09.002>
  • Emmerson Daniel P. G., Hems William P., Davis Benjamin G.: Carbohydrate-Derived Amino-Alcohol Ligands for Asymmetric Alkynylation of Aldehydes. Org Lett 2006, 8, 207. <http://dx.doi.org/10.1021/ol052503l>
  • Hargrave Jonathan D., Bish Gerwyn, Frost Christopher G.: Switching stereoselectivity in rhodium-catalysed 1,4-additions: the asymmetric synthesis of 2-substituted pyrrolizidinones. Chem Commun 2006, 4389. <http://dx.doi.org/10.1039/b610128c>
  • Eames Jason, Suggate Michael J.: Neue Entwicklungen bei der Chiralitätsübertragung in Enolatalkylierungen. Angew Chem 2005, 117, 190. <http://dx.doi.org/10.1002/ange.200461617>
  • Eames Jason, Suggate Michael J.: Recent Developments in the Transfer of Chirality within Enolate Alkylation Reactions. Angew Chem Int Ed 2005, 44, 186. <http://dx.doi.org/10.1002/anie.200461617>
  • Sibi Mukund P., Stanley Levi M.: Enantioselective diethylzinc additions to aldehydes catalyzed by chiral relay ligands. Tet Asymm 2004, 15, 3353. <http://dx.doi.org/10.1016/j.tetasy.2004.09.006>
  • Bull Steven D., Davies Stephen G., Garner A. Christopher, Savory Edward D., Snow Emma J., Smith Andrew D.: 2-Halo-diketopiperazines as chiral glycine cation equivalents. Tet Asymm 2004, 15, 3989. <http://dx.doi.org/10.1016/j.tetasy.2004.11.022>
  • Wakimoto Izumi, Tomioka Yuko, Kawanami Yasuhiro: Catalytic enantioselective conjugate addition of diethylzinc to chalcones using chiral amino alcohol–nickel complexes. Tetrahedron 2002, 58, 8095. <http://dx.doi.org/10.1016/S0040-4020(02)00994-8>
  • Quaranta Laura, Corminboeuf Olivier, Renaud Philippe: Chiral Relay Effect:  4-Substituted 1,3-Benzoxazol-2-(3H)-ones as Achiral Templates for Enantioselective Diels−Alder Reactions. Org Lett 2002, 4, 39. <http://dx.doi.org/10.1021/ol016966c>
  • Sibi Mukund P., Liu Mei: Enantioselective Conjugate Addition of Hydroxylamines to Pyrazolidinone Acrylamides. Org Lett 2001, 3, 4181. <http://dx.doi.org/10.1021/ol016807t>