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Chirale elektrophile Synthesebausteine mit vier verschiedenen funktionellen Gruppen aus Weinsäure, 2, 3‐ und 3, 4‐Epoxy‐butandiolderivate in allen vier stereoisomeren Formen
Author(s) -
Hungerbühler Ernst,
Seebach Dieter
Publication year - 1981
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19810640311
Subject(s) - chemistry , tartaric acid , enantiomer , epoxy , electrophile , diastereomer , reagent , epoxide , sharpless epoxidation , stereochemistry , organic chemistry , catalysis , citric acid
Chiral Electrophilic Synthetic Building Blocks with Four Different Functional Groups from Tartaric Acid, 2, 3‐ and 3, 4‐Epoxy‐butanediol Derivatives in All Four Stereoisomeric Forms Efficient and simple procedures have been developed for the preparation of the threo ‐ and erythro ‐3, 4‐epoxy‐1, 2‐butanediol derivatives 3 and 8 and of the cis ‐ and trans ‐2, 3‐epoxy‐1, 4‐butanediol derivatives 7 and 9 in both enantiomeric forms from tartaric acid (see Scheme 2 ). These epoxides should prove versatile as alkylating reagents in syntheses of enantiomerically pure natural products and of physiologically active compounds.