NUCLEOPHILIC ADDITIONS OF GRIGNARD-REAGENTS TO N-BENZYL-2,3-O-ISOPROPYLIDENE-D-GLYCERALDEHYDE NITRONE (BIGN) - SYNTHESIS OF (2S,3R) AND (2S,3S)-3-PHENYLISOSERINE

Authors
MERINO P CASTILLO E FRANCO S MERCHAN FL TEJERO T
Citation
P. Merino et al., NUCLEOPHILIC ADDITIONS OF GRIGNARD-REAGENTS TO N-BENZYL-2,3-O-ISOPROPYLIDENE-D-GLYCERALDEHYDE NITRONE (BIGN) - SYNTHESIS OF (2S,3R) AND (2S,3S)-3-PHENYLISOSERINE, Tetrahedron, 54(40), 1998, pp. 12301-12322
Citations number
55
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
40
Year of publication
1998
Pages
12301 - 12322
Database
ISI
SICI code
0040-4020(1998)54:40<12301:NAOGTN>2.0.ZU;2-X
Abstract
A remarkable Lewis acid tuning has been observed in the nucleophilic a ddition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2-O-isopropylidene-D-glyceraldehyde. The obtained alpha,beta-dialko xy hydroxylamines can serve as starting points for the synthesis of bo th aminodiols and alpha-hydroxy-beta-amino acids. This synthetic appro ach is illustrated by the synthesis of the antipode of the C-13 side c hain of Taxotere as well as its C-3 epimer. (C) 1998 Elsevier Science Ltd. All rights reserved.