Catalytic diastereoselective tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts by C-C bond cleavage

Wenguo Yang, Davin Tan, Richmond Lee, Lixin Li, Yuanhang Pan, Kuo-Wei Huang, Choonhong Tan, Zhiyong Jiang

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Through the cleavage of the C-C bond, the first catalytic tandem conjugate addition-elimination reaction of Morita-Baylis-Hillman C adducts has been presented. Various S N2′-like C-, S-, and P-allylic compounds could be obtained with exclusive E configuration in good to excellent yields. The Michael product could also be easily prepared by tuning the β-C-substituent group of the α-methylene ester under the same reaction conditions. Calculated relative energies of various transition states by DFT methods strongly support the observed chemoselectivity and diastereoselectivity. © 2012 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.
Original languageEnglish (US)
Pages (from-to)771-777
Number of pages7
JournalChemistry - An Asian Journal
Volume7
Issue number4
DOIs
StatePublished - Feb 8 2012

ASJC Scopus subject areas

  • Chemistry(all)

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