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Preparation of Optically Active Alcohols from 1,3‐Dioxan‐4‐ones. A Practical Version of the Asymmetric Synthesis with Nucleophilic Substitution at Acetal Centers
Author(s) -
Seebach Dieter,
Imwinkelried René,
Stucky Gerhard
Publication year - 1986
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198601781
Subject(s) - acetal , nucleophile , chemistry , alkoxy group , silylation , optically active , alcohol , nucleophilic substitution , base (topology) , substitution reaction , combinatorial chemistry , medicinal chemistry , organic chemistry , stereochemistry , catalysis , mathematical analysis , alkyl , mathematics
Aliphatic alcohols 3 in ≥90% ee may be prepared via the dioxanones 1 , which are readily accessible from aldehydes inexpensive ( R )‐3‐hydroxybutanoic acid. The cyclic acetals 1 react with silyl nucleophiles Me 3 SiR Nu in the presence of Cl 3 TiX to give, with ≥95% ds , the 3‐alkoxy acids 2 , from which the alcohols 3 are released by base‐induced elimination.