Pentanidium-catalyzed enantioselective phase-transfer conjugate addition reactions

Ting Ma; Xiao Fu; Choonwee Kee; Lili Zong; Yuanhang Pan; Kuo-Wei Huang; Choonhong Tan

doi:10.1021/ja1098353

Pentanidium-catalyzed enantioselective phase-transfer conjugate addition reactions

Ting Ma, Xiao Fu, Choonwee Kee, Lili Zong, Yuanhang Pan, Kuo-Wei Huang, Choonhong Tan

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

123 Scopus citations

Abstract

A new chiral entity, pentanidium, has been shown to be an excellent chiral phase-transfer catalyst. The enantioselective Michael addition reactions of tert-butyl glycinate-benzophenone Schiff base with various α,β- unsaturated acceptors provide adducts with high enantioselectivities. A successful gram-scale experiment at a low catalyst loading of 0.05 mol % indicates the potential for practical applications of this methodology. Phosphoglycine ester analogues can also be utilized as the Michael donor, affording enantioenriched α-aminophosphonic acid derivatives and phosphonic analogues of (S)-proline. © 2011 American Chemical Society.

Original language	English (US)
Pages (from-to)	2828-2831
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	9
DOIs	https://doi.org/10.1021/ja1098353
State	Published - Mar 9 2011

ASJC Scopus subject areas

Biochemistry
Colloid and Surface Chemistry
Chemistry(all)
Catalysis

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10.1021/ja1098353

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title = "Pentanidium-catalyzed enantioselective phase-transfer conjugate addition reactions",

abstract = "A new chiral entity, pentanidium, has been shown to be an excellent chiral phase-transfer catalyst. The enantioselective Michael addition reactions of tert-butyl glycinate-benzophenone Schiff base with various α,β- unsaturated acceptors provide adducts with high enantioselectivities. A successful gram-scale experiment at a low catalyst loading of 0.05 mol % indicates the potential for practical applications of this methodology. Phosphoglycine ester analogues can also be utilized as the Michael donor, affording enantioenriched α-aminophosphonic acid derivatives and phosphonic analogues of (S)-proline. {\textcopyright} 2011 American Chemical Society.",

author = "Ting Ma and Xiao Fu and Choonwee Kee and Lili Zong and Yuanhang Pan and Kuo-Wei Huang and Choonhong Tan",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by a research grant (R-143-000-342-112) and a scholarship (to M.T.) from NUS.",

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T1 - Pentanidium-catalyzed enantioselective phase-transfer conjugate addition reactions

AU - Ma, Ting

AU - Fu, Xiao

AU - Kee, Choonwee

AU - Zong, Lili

AU - Pan, Yuanhang

AU - Huang, Kuo-Wei

AU - Tan, Choonhong

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by a research grant (R-143-000-342-112) and a scholarship (to M.T.) from NUS.

PY - 2011/3/9

Y1 - 2011/3/9

N2 - A new chiral entity, pentanidium, has been shown to be an excellent chiral phase-transfer catalyst. The enantioselective Michael addition reactions of tert-butyl glycinate-benzophenone Schiff base with various α,β- unsaturated acceptors provide adducts with high enantioselectivities. A successful gram-scale experiment at a low catalyst loading of 0.05 mol % indicates the potential for practical applications of this methodology. Phosphoglycine ester analogues can also be utilized as the Michael donor, affording enantioenriched α-aminophosphonic acid derivatives and phosphonic analogues of (S)-proline. © 2011 American Chemical Society.

AB - A new chiral entity, pentanidium, has been shown to be an excellent chiral phase-transfer catalyst. The enantioselective Michael addition reactions of tert-butyl glycinate-benzophenone Schiff base with various α,β- unsaturated acceptors provide adducts with high enantioselectivities. A successful gram-scale experiment at a low catalyst loading of 0.05 mol % indicates the potential for practical applications of this methodology. Phosphoglycine ester analogues can also be utilized as the Michael donor, affording enantioenriched α-aminophosphonic acid derivatives and phosphonic analogues of (S)-proline. © 2011 American Chemical Society.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 9

ER -

Pentanidium-catalyzed enantioselective phase-transfer conjugate addition reactions

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CCDC 836213: Experimental Crystal Structure Determination : (S,S)-2-((1,3-Dimethyl-4,5-diphenylimidazolidin-2-ylidene)amino)-1,3-dimethyl-4,5-diphenyl-4,5-dihydro-1H-imidazol-3-ium chloride ethyl acetate solvate monohydrate

CCDC 836212: Experimental Crystal Structure Determination : (2R,3S)-t-Butyl 3-(4-chlorophenyl)-5-phenyl-3,4-dihydro-2H-pyrrole-2-carboxylate

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Pentanidium-catalyzed enantioselective phase-transfer conjugate addition reactions

Abstract

ASJC Scopus subject areas

Access to Document

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CCDC 836213: Experimental Crystal Structure Determination : (S,S)-2-((1,3-Dimethyl-4,5-diphenylimidazolidin-2-ylidene)amino)-1,3-dimethyl-4,5-diphenyl-4,5-dihydro-1H-imidazol-3-ium chloride ethyl acetate solvate monohydrate

CCDC 836212: Experimental Crystal Structure Determination : (2R,3S)-t-Butyl 3-(4-chlorophenyl)-5-phenyl-3,4-dihydro-2H-pyrrole-2-carboxylate

Cite this