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

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)]


Published in:
Tetrahedron Letters, 38, 10, 1771-1772
Year:
1997
Keywords:
Note:
CAN 126:264329
34-2
Amino Acids, Peptides, and Proteins
Inst. Chimie Substances Naturelles,CNRS,Gif-Sur-Yvette,Fr.
Journal
0040-4039
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.)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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