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