Asymmetric catalytic aza-Morita-Baylis-Hillman reaction using chiral bifunctional phosphine amides as catalysts

Ming Juan Qi, Teng Ai, Min Shi, Guigen Li

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72 Scopus citations

Abstract

The asymmetric catalytic aza-Morita-Baylis-Hillman reaction of N-sulfonated imines with α,β-unsaturated ketones has been successfully conducted by using chiral bifunctional phosphine amides as catalysts. A series of new chiral bifunctional phosphine amides were designed, synthesized, and systematically studied for this asymmetric reaction. The corresponding aza-MBH adducts were obtained in good yields (75-99%) and up to very good enantiomeric excesses (51-95% ee) under mild conditions.

Original languageEnglish (US)
Pages (from-to)1181-1186
Number of pages6
JournalTetrahedron
Volume64
Issue number7
DOIs
StatePublished - Feb 11 2008

Bibliographical note

Funding Information:
We thank the Robert Welch Foundation (to G.L., D-1361, USA), the Shanghai Municipal Committee of Science and Technology (to M.S., 04JC14083, 06XD14005, PR China), Chinese Academy of Sciences (to M.S., KGCX2-210-01), and the National Natural Science Foundation of China for financial support (M.S., 20472096, 203900502, 20672127, and 20732008).

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