L-Threonine-derived novel bifunctional phosphine-sulfonamide catalyst-promoted enantioselective aza-morita-Baylis-Hillman reaction

Fangrui Zhong; Youqing Wang; Xiaoyu Han; Kuo-Wei Huang; Yixin Lu

doi:10.1021/ol103145g

L-Threonine-derived novel bifunctional phosphine-sulfonamide catalyst-promoted enantioselective aza-morita-Baylis-Hillman reaction

Fangrui Zhong, Youqing Wang, Xiaoyu Han, Kuo-Wei Huang, Yixin Lu

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

100 Scopus citations

Abstract

A series of novel bifunctional phosphine-sulfonamide organic catalysts were designed and readily prepared from natural amino acids, and they were utilized to promote enantioselective aza-Morita-Baylis-Hillman (MBH) reactions. l-Threonine-derived phosphine-sulfonamide 9b was found to be the most efficient catalyst, affording the desired aza-MBH adducts in high yields and with excellent enantioselectivities. © 2011 American Chemical Society.

Original language	English (US)
Pages (from-to)	1310-1313
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	6
DOIs	https://doi.org/10.1021/ol103145g
State	Published - Mar 18 2011

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: We are grateful for the generous financial support from the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112) to Y.L. and from King Abdullah University of Science and Technology to K.-W.H.

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

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10.1021/ol103145g

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title = "L-Threonine-derived novel bifunctional phosphine-sulfonamide catalyst-promoted enantioselective aza-morita-Baylis-Hillman reaction",

abstract = "A series of novel bifunctional phosphine-sulfonamide organic catalysts were designed and readily prepared from natural amino acids, and they were utilized to promote enantioselective aza-Morita-Baylis-Hillman (MBH) reactions. l-Threonine-derived phosphine-sulfonamide 9b was found to be the most efficient catalyst, affording the desired aza-MBH adducts in high yields and with excellent enantioselectivities. {\textcopyright} 2011 American Chemical Society.",

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note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We are grateful for the generous financial support from the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112) to Y.L. and from King Abdullah University of Science and Technology to K.-W.H.",

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AU - Han, Xiaoyu

AU - Huang, Kuo-Wei

AU - Lu, Yixin

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We are grateful for the generous financial support from the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112) to Y.L. and from King Abdullah University of Science and Technology to K.-W.H.

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N2 - A series of novel bifunctional phosphine-sulfonamide organic catalysts were designed and readily prepared from natural amino acids, and they were utilized to promote enantioselective aza-Morita-Baylis-Hillman (MBH) reactions. l-Threonine-derived phosphine-sulfonamide 9b was found to be the most efficient catalyst, affording the desired aza-MBH adducts in high yields and with excellent enantioselectivities. © 2011 American Chemical Society.

AB - A series of novel bifunctional phosphine-sulfonamide organic catalysts were designed and readily prepared from natural amino acids, and they were utilized to promote enantioselective aza-Morita-Baylis-Hillman (MBH) reactions. l-Threonine-derived phosphine-sulfonamide 9b was found to be the most efficient catalyst, affording the desired aza-MBH adducts in high yields and with excellent enantioselectivities. © 2011 American Chemical Society.

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L-Threonine-derived novel bifunctional phosphine-sulfonamide catalyst-promoted enantioselective aza-morita-Baylis-Hillman reaction

Abstract

Bibliographical note

ASJC Scopus subject areas

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