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

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

doi:10.1016/j.tet.2007.11.039

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

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

Center for Drug Design

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	1181-1186
Number of pages	6
Journal	Tetrahedron
Volume	64
Issue number	7
DOIs	https://doi.org/10.1016/j.tet.2007.11.039
State	Published - 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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10.1016/j.tet.2007.11.039

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title = "Asymmetric catalytic aza-Morita-Baylis-Hillman reaction using chiral bifunctional phosphine amides as catalysts",

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.",

author = "Qi, {Ming Juan} and Teng Ai and Min Shi and Guigen Li",

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). ",

year = "2008",

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doi = "10.1016/j.tet.2007.11.039",

language = "English (US)",

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AU - Qi, Ming Juan

AU - Ai, Teng

AU - Shi, Min

AU - Li, Guigen

N1 - 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).

PY - 2008/2/11

Y1 - 2008/2/11

N2 - 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.

AB - 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.

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JO - Tetrahedron

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

Abstract

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