Highly Regio-, Diastereo-, and Enantioselective Rhodium-Catalyzed Intramolecular Cyclopropanation of (Z)-1,3-Dienyl Aryldiazoacetates.

Author(s) Marichev, K.O.; Ramey, J.T.; Arman, H.; Doyle, M.P.
Journal Org Lett
Date Published 2017 Mar 01
Abstract

Chiral cyclopenta[2,3]cyclopropa[1,2-c]pyran-4-ones have been synthesized via dirhodium(II)-catalyzed intramolecular cyclopropanation of (Z)-1,3-dienyl aryldiazoacetates. High regio-, diastereo-, and enantiocontrol were achieved using chiral dirhodium 2-phthalimide carboxylates. Preferential addition occurs at the 3,4- rather than the 1,2-double bond with the chiral dirhodium catalysts, although both outcomes occur with other transition-metal catalysts.

DOI 10.1021/acs.orglett.7b00119
ISSN 1523-7052
Citation Marichev KO, Ramey JT, Arman H, Doyle MP. Highly Regio-, Diastereo-, and Enantioselective Rhodium-Catalyzed Intramolecular Cyclopropanation of (Z)-1,3-Dienyl Aryldiazoacetates. Org Lett. 2017.

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