Preparation of Optically Active Alcohols from 1,3‐Dioxan‐4‐ones. A Practical Version of the Asymmetric Synthesis with Nucleophilic Substitution at Acetal Centers | Zendy

Seebach Dieter | Zendy; Imwinkelried René | Zendy; Stucky Gerhard | Zendy

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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.

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