THE TETRAHYDROOXAZINONE WAY TO ENANTIOPURE ALPHA-AMINO-ACIDS - SYNTHESIS OF CIS AND TRANS 3-VINYL PIPECOLIC ACIDS VIA AN INTRAMOLECULAR REACTION BETWEEN AN IMINIUM ION AND AN ALLYLSILANE MOIETIES

Authors
AGAMI C BIHAN D HAMON L PUCHOTKADOURI C
Citation
C. Agami et al., THE TETRAHYDROOXAZINONE WAY TO ENANTIOPURE ALPHA-AMINO-ACIDS - SYNTHESIS OF CIS AND TRANS 3-VINYL PIPECOLIC ACIDS VIA AN INTRAMOLECULAR REACTION BETWEEN AN IMINIUM ION AND AN ALLYLSILANE MOIETIES, Tetrahedron, 54(35), 1998, pp. 10309-10316
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
35
Year of publication
1998
Pages
10309 - 10316
Database
ISI
SICI code
0040-4020(1998)54:35<10309:TTWTEA>2.0.ZU;2-A
Abstract
Reaction of glyoxal with a derivative of (R)-phenylglycinol having an allylsilane side-chain afforded a transient iminium ion. Intramolecula r reaction of the iminium ion and the allylsilane moieties occurred in a totally stereoselective way. Straightforward transformations ultima tely led to enantiopure either cis or trans 3-vinyl pipecolic acid met hyl ester. The stereochemical course of this reaction was rationalized via AMI calculations. (C) 1998 Elsevier Science Ltd. All rights reser ved.