Premium
Synthesis of Optically Active Butenolides and γ‐Lactones by the Sharpless Asymmetric Dihydroxylation of β,γ‐Unsaturated Carboxylic Esters
Author(s) -
Harcken Christian,
Brückner Reinhard
Publication year - 1997
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.199727501
Subject(s) - sharpless asymmetric dihydroxylation , chemistry , dihydroxylation , enantiomer , optically active , alkyl , stereochemistry , enantioselective synthesis , lactone , organic chemistry , catalysis
Deconjugated esters 1 and AD mix α or AD mix β give cis‐configured γ‐alkyl‐β‐hydroxy‐γ‐lactones 2 . They are versatile precursors for γ‐chiral butenolides and γ‐chiral butyrolactones of moderate to high enantiomeric purity, as shown through their conversion into the natural products 3 (92% ee), 4 (95% ee), 5 (97% ee), and 6 (78% ee).