Novel α-amino acid-derived phase-transfer catalyst application to a highly enantio- and diastereoselective nitro-Mannich reaction

Yuxin Liu; Zhonglin Wei; Yu Liu; Jungang Cao; Dapeng Liang; Yingjie Lin; Haifeng Duan

doi:10.1039/c7ob02501g

Novel α-amino acid-derived phase-transfer catalyst application to a highly enantio- and diastereoselective nitro-Mannich reaction

Organic & Biomolecular Chemistry ◽

10.1039/c7ob02501g ◽

2017 ◽

Vol 15 (43) ◽

pp. 9234-9242 ◽

Cited By ~ 8

Author(s):

Yuxin Liu ◽

Zhonglin Wei ◽

Yu Liu ◽

Jungang Cao ◽

Dapeng Liang ◽

...

Keyword(s):

Amino Acid ◽

Mannich Reaction ◽

Phase Transfer ◽

Phase Transfer Catalyst

Very broad substrate generality was observed, and the products were achieved in high enantio-/diastereoselectivities (90–>99.9% ee, 9 : 1 to 11 : 1 dr).

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The asymmetric vinylogous Mannich reaction of noncyclic dicyanoolefins catalyzed by a bifunctional thiourea–ammonium salt phase transfer catalyst

New Journal of Chemistry ◽

10.1039/c9nj01635j ◽

2019 ◽

Vol 43 (25) ◽

pp. 10012-10016

Author(s):

Yanhong Fang ◽

Zhonglin Wei ◽

Ying Wang ◽

Shuo Liu ◽

Jungang Cao ◽

...

Keyword(s):

Ammonium Salt ◽

Mannich Reaction ◽

Phase Transfer ◽

Phase Transfer Catalyst ◽

Salt Phase

An efficient enantioselective vinylogous Mannich reaction of N-Boc aminosulfones with noncyclic α,α-dicyanoolefins has been realized using an extraordinary bifunctional thiourea–ammonium salt phase transfer catalyst derived from quinine.

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Effective asymmetric vinylogous Mannich reaction of isatin imines with α,α-dicyanoolefins in the presence of a simple chiral amide phosphonium bifunctional phase transfer catalyst

Organic Chemistry Frontiers ◽

10.1039/c6qo00546b ◽

2017 ◽

Vol 4 (1) ◽

pp. 101-114 ◽

Cited By ~ 27

Author(s):

Cang Cheng ◽

Xuehe Lu ◽

Luo Ge ◽

Jie Chen ◽

Weiguo Cao ◽

...

Keyword(s):

Mannich Reaction ◽

Phase Transfer ◽

Oxidative Cleavage ◽

Phase Transfer Catalyst

A Mannich reaction between N-Boc isatin imine and α,α-dicyanoolefin as well as subsequent oxidative cleavage of the malonic nitrile moiety were described.

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Highly enantioselective nitro-Mannich reaction of ketimines under phase-transfer catalysis

Organic Chemistry Frontiers ◽

10.1039/c7qo00124j ◽

2017 ◽

Vol 4 (7) ◽

pp. 1266-1271 ◽

Cited By ~ 21

Author(s):

Bin Wang ◽

Tong Xu ◽

Lei Zhu ◽

Yu Lan ◽

Jingdong Wang ◽

...

Keyword(s):

Density Functional Theory ◽

Dft Calculations ◽

Transition State ◽

Mannich Reaction ◽

Density Functional ◽

Phase Transfer Catalysis ◽

Phase Transfer ◽

Phase Transfer Catalyst ◽

Protecting Group ◽

Functional Theory

A novel bifunctional phase-transfer catalyst 1i was found to be highly efficient for the nitro-Mannich reaction of unactivated ketone-derived imines with the introduction of the protecting group 6-methyl-2-pyridylsulfonyl to the ketimines. Density functional theory (DFT) calculations are also performed to give the possible transition-state model.

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Ir/PTC cooperatively catalyzed asymmetric umpolung allylation of α-imino ester enabled synthesis of α-quaternary amino acid derivatives bearing two vicinal stereocenters

Chemical Communications ◽

10.1039/c6cc09654a ◽

2017 ◽

Vol 53 (12) ◽

pp. 1985-1988 ◽

Cited By ~ 37

Author(s):

Yong-Liang Su ◽

Yu-Hui Li ◽

Yu-Gen Chen ◽

Zhi-Yong Han

Keyword(s):

Amino Acid ◽

Phase Transfer ◽

Phase Transfer Catalyst ◽

Amino Acid Derivatives ◽

Imino Esters

A novel Ir/PTC (phase-transfer catalyst) cooperatively catalyzed asymmetric umpolung allylation of simple α-imino esters is developed and it provides facile access to α-quaternary amino acid derivatives bearing two vicinal stereocenters.

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