A Sequential Pd-AAA/Cross-Metathesis/Cope Rearrangement Strategy for the Stereoselective Synthesis of Chiral Butenolides | Zendy

Sidonie Aubert | Zendy; Tania Katsina | Zendy; Stellios Arseniyadis | Zendy

Open Access

A Sequential Pd-AAA/Cross-Metathesis/Cope Rearrangement Strategy for the Stereoselective Synthesis of Chiral Butenolides

Author(s) -

Sidonie Aubert,

Tania Katsina,

Stellios Arseniyadis

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b00521

Subject(s) - stereocenter , chemistry , metathesis , sigmatropic reaction , stereoselectivity , cope rearrangement , tsuji–trost reaction , allylic rearrangement , palladium , stereochemistry , salt metathesis reaction , furan , combinatorial chemistry , ring closing metathesis , catalysis , enantioselective synthesis , organic chemistry , polymerization , polymer

A practical and highly enantio- (up to 94:6 er) and diastereoselective (up to >20:1 dr) synthesis of γ-butenolides bearing two adjacent stereogenic centers is reported featuring a sequential direct palladium-catalyzed asymmetric allylic alkylation/( E)-selective cross-metathesis/[3,3]-sigmatropic Cope rearrangement from readily available α-substituted (5 H)-furan-2-ones.

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