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Titolo:
2-lithio-N-BOC-thiazolidines as chiral acyl anion synthons: evaluation of facial stereoselectivity in the addition of chiral organolithiums to aldehydes
Autore:
Gawley, RE; Zhang, QH; McPhail, AT;
Indirizzi:
Univ Miami, Dept Chem, Coral Gables, FL 33124 USA Univ Miami Coral GablesFL USA 33124 ept Chem, Coral Gables, FL 33124 USA Duke Univ, Dept Chem, Durham, NC 27706 USA Duke Univ Durham NC USA 27706Duke Univ, Dept Chem, Durham, NC 27706 USA
Titolo Testata:
TETRAHEDRON-ASYMMETRY
fascicolo: 10, volume: 11, anno: 2000,
pagine: 2093 - 2106
SICI:
0957-4166(20000602)11:10<2093:2ACAAS>2.0.ZU;2-Y
Fonte:
ISI
Lingua:
ENG
Soggetto:
LITHIOAMINE SYNTHETIC EQUIVALENTS; DIPOLE-STABILIZED CARBANIONS; ASYMMETRIC CARBONYL ADDITION; ALPHA-AMINO CARBANIONS; ELECTROPHILIC SUBSTITUTION; ENANTIOSELECTIVE SYNTHESES; DEPROTONATIONS; STEREOCHEMISTRY; (-)-SPARTEINE; STEREOISOMERS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
51
Recensione:
Indirizzi per estratti:
Indirizzo: Gawley, RE Univ Miami, Dept Chem, Coral Gables, FL 33124 USA Univ Miami Coral Gables FL USA 33124 oral Gables, FL 33124 USA
Citazione:
R.E. Gawley et al., "2-lithio-N-BOC-thiazolidines as chiral acyl anion synthons: evaluation of facial stereoselectivity in the addition of chiral organolithiums to aldehydes", TETRAHEDR-A, 11(10), 2000, pp. 2093-2106

Abstract

Deprotonation of N-BOC-thiazolidines having an isopropyl group in the 4- or 5-position affords chiral organolithiums that add to aldehydes in excellent yields. The relative and absolute configurations at both new stereocenters of the major and minor isomers were deduced. Mechanistic considerations suggest that each organolithium adds with a high degree of diastereoselectivity. We also demonstrated, as proof of principle, that further elaborationof the addition products into alpha-hydroxyaldehydes and glycols can be achieved. (C) 2000 Elsevier Science Ltd. All rights reserved.

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Documento generato il 25/01/20 alle ore 16:40:23