Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones

Guanghu Tong, Bo Zhu, Richmond Lee, Wenguo Yang, Davin Tan, Caiyun Yang, Zhiqiang Han, Lin Yan, Kuo-Wei Huang, Zhiyong Jiang

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

The asymmetric allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates with allyl ketones has been developed. The α-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared. © 2013 American Chemical Society.
Original languageEnglish (US)
Pages (from-to)5067-5072
Number of pages6
JournalJournal of Organic Chemistry
Volume78
Issue number10
DOIs
StatePublished - Apr 26 2013

ASJC Scopus subject areas

  • Organic Chemistry

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