research article

A highly stereoselective synthesis of (2S, 3S)-beta -hydroxyleucine

Laib, Taoues
•
Chastanet, Jacqueline
•
Zhu, Jieping  
1997
Tetrahedron Letters

An efficient asym. synthesis of (2S,3S)-beta -hydroxyleucine is described. The key step in the synthesis was a highly diastereoselective nucleophilic addn. of Grignard reagent to N,N-dibenzyl-O-TBS-serinal (TBS = SiMe2CMe3). This strategy should be applicable to the synthesis of other related beta -hydroxy amino acids. [on SciFinder (R)]

Type
research article
DOI
10.1016/S0040-4039(97)00207-4
Author(s)
Laib, Taoues
Chastanet, Jacqueline
Zhu, Jieping  
Date Issued

1997

Publisher

Elsevier

Published in
Tetrahedron Letters
Volume

38

Issue

10

Start page

1771

End page

1772

Subjects

Amino acids Role: SPN (Synthetic preparation)

•

PREP (Preparation) (hydroxy; asym. synthesis of hydroxyleucine via stereoselective Grignard addn.); Asymmetric synthesis and induction (of hydroxyleucine via stereoselective Grignard addn.); Grignard reaction (stereoselective; asym. synthesis of hydroxyleucine via stereoselective Grignard addn.)

•

asym synthesis hydroxyleucine; leucine hydroxy asym synthesis; hydroxy amino acid asym synthesis; stereoselective Grignard amino aldehyde

Note

CAN 126:264329

34-2

Amino Acids, Peptides, and Proteins

Inst. Chimie Substances Naturelles,CNRS,Gif-Sur-Yvette,Fr.

Journal

written in English.

1068-55-9 (Isopropylmagnesium chloride); 188802-06-4 Role: RCT (Reactant), RACT (Reactant or reagent) (asym. synthesis of hydroxyleucine via stereoselective Grignard addn.); 125473-34-9P; 188802-09-7P; 188802-11-1P; 188802-13-3P; 188802-16-6P; 188840-00-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. synthesis of hydroxyleucine via stereoselective Grignard addn.); 188839-98-7P Role: SPN (Synthetic preparation), PREP (Preparation) (asym. synthesis of hydroxyleucine via stereoselective Grignard addn.)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LSPN  
Available on Infoscience
November 25, 2010
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/58547