Phosphine-Catalyzed [8 + 2]-Annulation of Heptafulvenes with Allenoates and Its Asymmetric Variant: Construction of Bicyclo[5.3.0]decane Scaffold

Zhenzhen Gao; Chang Wang; Leijie Zhou; Chunhao Yuan; Yumei Xiao; Hongchao Guo

doi:10.1021/acs.orglett.8b01734

Phosphine-Catalyzed [8 + 2]-Annulation of Heptafulvenes with Allenoates and Its Asymmetric Variant: Construction of Bicyclo[5.3.0]decane Scaffold

Org Lett. 2018 Jul 20;20(14):4302-4305. doi: 10.1021/acs.orglett.8b01734. Epub 2018 Jul 3.

Authors

Zhenzhen Gao^{1

2}, Chang Wang¹, Leijie Zhou¹, Chunhao Yuan¹, Yumei Xiao¹, Hongchao Guo^{1

3}

Affiliations

¹ Department of Applied Chemistry , China Agricultural University , Beijing 100193 , P. R. China.
² School of Pharmacy , Liaocheng University , Liaocheng 252000 , Shandong , P. R. China.
³ State Key Laboratory of Chemical Resource Engineering , Beijing University of Chemical Technology , Beijing 100029 , P. R. China.

PMID: 29969278
DOI: 10.1021/acs.orglett.8b01734

Abstract

In this paper, a phosphine-catalyzed [8 + 2]-annulation of heptafulvene with allenoates has been achieved under mild conditions, giving functionalized bicyclo[5.3.0]decane derivatives in moderate to excellent yields. Using chiral phosphine as the catalyst, optically active products were obtained in moderate to high yields with excellent enantioselectivities.

Publication types

Research Support, Non-U.S. Gov't