ChemInform Abstract: Stereoselective Synthesis of syn-α-Methyl-β-hydroxy Esters.

6533b820fe1ef96bd127994f

RESEARCH PRODUCT

ChemInform Abstract: Stereoselective Synthesis of syn-α-Methyl-β-hydroxy Esters.

Miguel Carda J. Alberto Marco Juan Murga Florenci V. González Eva Falomir

subject

chemistry.chemical_classification Addition reaction chemistry.chemical_compound Ketone Enantiopure drug chemistry Aldol reaction Stereochemistry Propionate Stereoselectivity Erythrulose General Medicine Adduct

description

Abstract Boron enolates of an ethyl ketone structurally related to erythrulose react with achiral aldehydes in a highly stereoselective fashion to yield 1,2- syn /1,3- syn stereoisomers. Oxidative cleavage of the aldol adducts yields enantiopure O -formylated syn -α-methyl-β-hydroxy esters, easily cleaved to the corresponding hydroxyl-free compounds. The aforementioned ketone behaves therefore as a chiral propionate enolate equivalent.

year	journal	country	edition	language
2000-12-19	ChemInform

https://doi.org/10.1002/chin.200051034

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