STEREOCONTROLLED SYNTHESIS OF ALPHA,ALPHA-DISUBSTITUTED ALPHA-AMINOALDEHYDES AND ALPHA-AMINO-ACIDS USING A [3,3]ALLYLIC TRICHLORACETIMIDATEREARRANGEMENT

Authors
IMOGAI H PETIT Y LARCHEVEQUE M
Citation
H. Imogai et al., STEREOCONTROLLED SYNTHESIS OF ALPHA,ALPHA-DISUBSTITUTED ALPHA-AMINOALDEHYDES AND ALPHA-AMINO-ACIDS USING A [3,3]ALLYLIC TRICHLORACETIMIDATEREARRANGEMENT, Tetrahedron letters, 37(15), 1996, pp. 2573-2576
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
15
Year of publication
1996
Pages
2573 - 2576
Database
ISI
SICI code
0040-4039(1996)37:15<2573:SSOAA>2.0.ZU;2-G
Abstract
Sigmatropic rearrangement of trichloracetimidates derived from syn mon oprotected allylic diols 3 resulting from the condensation of vinylala nes or cuprates with alpha-alkoxyaldehydes afforded diastereomerically pure allylic amines 6. The oxidative cleavage of these amines allowed the access to alpha,alpha-disubstituted alpha-aminoacids in high enan tiomeric purity. Copyright (C) 1996 Published by Elsevier Science Ltd