Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates

Wenguo Yang, Davin Tan, Lixin Li, Zhiqiang Han, Lin Yan, Kuo-Wei Huang, Choonhong Tan, Zhiyong Jiang

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

The asymmetric allylic alkenylation of Morita-Baylis-Hillman (MBH) carbonates with N-itaconimides as nucleophiles has been developed using a commercially available Cinchona alkaloid catalyst. A variety of multifunctional chiral α-methylene-β-maleimide esters were attained in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 91% ee). The origin of the regio- and stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed regio- and enantioselectivity. © 2012 American Chemical Society.
Original languageEnglish (US)
Pages (from-to)6600-6607
Number of pages8
JournalThe Journal of Organic Chemistry
Volume77
Issue number15
DOIs
StatePublished - Jul 26 2012

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates'. Together they form a unique fingerprint.

Cite this