Diastereoselective Synthesis of gamma -Hydroxy-beta -Amino Alcohols and (2S,3S)-beta -Hydroxyleucine from Chiral D-(N,N-Dibenzylamino)serine (TBDMS) Aldehyde

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)]


Publié dans:
Journal of Organic Chemistry, 63, 5, 1709-1713
Année
1998
Mots-clefs:
Note:
CAN 128:154357
34-2
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
0022-3263
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)
Laboratoires:




 Notice créée le 2010-11-25, modifiée le 2018-09-13


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