Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water

Bo Zhu, Lin Yan, Yuanhang Pan, Richmond Lee, Hongjun Liu, Zhiqiang Han, Kuo-Wei Huang, Choonhong Tan, Zhiyong Jiang

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using 18O-labeling experiments. © 2011 American Chemical Society.
Original languageEnglish (US)
Pages (from-to)6894-6900
Number of pages7
JournalThe Journal of Organic Chemistry
Volume76
Issue number16
DOIs
StatePublished - Aug 19 2011

ASJC Scopus subject areas

  • Organic Chemistry

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