Phosphine-catalyzed cascade [3 + 2] cyclization-allylic alkylation, [2 + 2 + 1] annulation, and [3 + 2] cyclization reactions between allylic carbonates and enones

Rong Zhou; Jianfang Wang; Haibin Song; Zhengjie He

doi:10.1021/ol102738b

Phosphine-catalyzed cascade [3 + 2] cyclization-allylic alkylation, [2 + 2 + 1] annulation, and [3 + 2] cyclization reactions between allylic carbonates and enones

Org Lett. 2011 Feb 18;13(4):580-3. doi: 10.1021/ol102738b. Epub 2011 Jan 14.

Authors

Rong Zhou¹, Jianfang Wang, Haibin Song, Zhengjie He

Affiliation

¹ The State Key Laboratory of Elemento-Organic Chemistry and Department of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300071, P.R. China.

PMID: 21235263
DOI: 10.1021/ol102738b

Abstract

The phosphine-catalyzed annulations between Morita-Baylis-Hillman adduct carbonates and enones are reported. Under the catalysis of PBu(3) (20 mol %), cascade [3 + 2] cyclization-allylic alkylation, [2 + 2 + 1] annulation, and [3 + 2] cyclization reactions chemoselectively occur depending on the substituent variation of both the carbonate and enone. These reactions provide efficient syntheses of highly functionalized cyclopentenes and cyclopentanes.