Diastereoselective Synthesis of gamma -Hydroxy-beta -Amino Alcohols and (2S,3S)-beta -Hydroxyleucine from Chiral D-(N,N-Dibenzylamino)serine (TBDMS) Aldehyde
Laieb, Taoues; Chastanet, Jacqueline; Zhu, Jieping
1998

Abstract

Title serine deriv. I (TBDMS = tert-butyldimethylsilyl; Bn = benzyl) was synthesized from D-serine in excellent overall yield. The reactions of I with Grignard and organocerium reagents were highly stereoselective (Felkin model) to give gamma -hydroxy-beta -amino alcs. II (R = CHMe2, Me, Ph, Bu) in good yield. Transformation of II (R = CHMe2) into (2S,3S)-beta -hydroxyleucine (III) is also reported. [on SciFinder (R)]

Details

Title Diastereoselective Synthesis of gamma -Hydroxy-beta -Amino Alcohols and (2S,3S)-beta -Hydroxyleucine from Chiral D-(N,N-Dibenzylamino)serine (TBDMS) Aldehyde
Author(s) Laieb, Taoues ; Chastanet, Jacqueline ; Zhu, Jieping
Published in Journal of Organic Chemistry
Volume 63
Issue 5
Pages 1709-1713
Date 1998
ISSN 0022-3263
Keywords
Alcohols Role: SPN (Synthetic preparation); PREP (Preparation) (amino; hydroxy; diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); Glycols Role: SPN (Synthetic preparation); PREP (Preparation) (amino; diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); Asymmetric synthesis and induction (diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); Addition reaction; Addition reaction (nucleophilic; stereoselective; diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); asym synthesis hydroxy amino alc; stereoselective Grignard dibenzylserine aldehyde prepn; organocerium stereoselective addn dibenzylserine aldehyde prepn
Note CAN 128:154357
34-2
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
24184-43-8 (D-Serine methyl ester) Role: RCT (Reactant), RACT (Reactant or reagent) (diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); 188802-06-4P; 188802-09-7P; 188802-11-1P; 188802-13-3P; 188802-16-6P; 188840-00-8P; 202478-34-0P; 202478-35-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); 188839-98-7P; 202478-36-2P; 202478-37-3P; 202478-38-4P Role: SPN (Synthetic preparation), PREP (Preparation) (diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde)
DOI https://doi.org/10.1021/jo971468w
Laboratories LSPN
Record Appears in Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date 2010-11-25