Synthesis of Optically Active Butenolides and γ‐Lactones by the Sharpless Asymmetric Dihydroxylation of β,γ‐Unsaturated Carboxylic Esters | Zendy

Harcken Christian | Zendy; Brückner Reinhard | Zendy

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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).

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