research article

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
The Journal of Organic Chemistry

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)]

Type
research article
DOI
10.1021/jo971468w
Author(s)
Laieb, Taoues
Chastanet, Jacqueline
Zhu, Jieping  
Date Issued

1998

Published in
The Journal of Organic Chemistry
Volume

63

Issue

5

Start page

1709

End page

1713

Subjects

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)

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/20.500.14299/58537