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Enantioselective catalytic transannular ketone-ene reactions.

ABSTRACT: Highly enantio- and diastereoselective transannular ketone-ene reactions are catalyzed by a new chromium(III) triflate tridentate Schiff base complex. Electronically unactivated keto-olefins undergo heteroene reactions at ambient temperature to afford enantioenriched bicyclic alcohols, common structural motifs in natural products. The kinetic resolution of a configurationally stable planar-chiral cyclodecenone is also described.

SUBMITTER: Rajapaksa NS

PROVIDER: S-EPMC3799808 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature

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Enantioselective catalytic transannular ketone-ene reactions.

Rajapaksa Naomi S NS Jacobsen Eric N EN

Organic letters 20130808 16

Highly enantio- and diastereoselective transannular ketone-ene reactions are catalyzed by a new chromium(III) triflate tridentate Schiff base complex. Electronically unactivated keto-olefins undergo heteroene reactions at ambient temperature to afford enantioenriched bicyclic alcohols, common structural motifs in natural products. The kinetic resolution of a configurationally stable planar-chiral cyclodecenone is also described. ...[more]

PMID: 23923982

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