Asymmetric synthesis of β-amino ketones by using cinchona alkaloid-based chiral phase transfer catalysts

A highly enantioselective nucleophilic addition of ketones to versatile imines catalyzed by chiral PTC has been developed, and the process affords the Mannich reaction products with tertiary stereocenters in good to high yields and excellent enantioselectivities. This protocol is effective for gram scale reaction.

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9-Amino-(9-deoxy)cinchona alkaloid-derived new chiral phase-transfer catalysts

Organic & Biomolecular Chemistry ◽

10.1039/c4ob01648c ◽

2014 ◽

Vol 12 (41) ◽

pp. 8336-8345 ◽

Cited By ~ 10

Author(s):

Wenwen Peng ◽

Jingwei Wan ◽

Bing Xie ◽

Xuebing Ma

Keyword(s):

Schiff Base ◽

Phase Transfer ◽

Cinchona Alkaloid ◽

Chiral Phase ◽

Phase Transfer Catalysts ◽

Chiral Phase Transfer Catalysts ◽

High Yields

9-Amino-(9-deoxy)cinchona alkaloid-derived chiral phase-transfer catalysts achieved high yields (92–99%) and excellent enantioselectivities (87–96% ee) in the enantioselective α-alkylation of glycine Schiff base.

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Asymmetric synthesis of α-amino acids using polymer-supported Cinchona alkaloid-derived ammonium salts as chiral phase-transfer catalysts

Tetrahedron Asymmetry ◽

10.1016/s0957-4166(00)00317-7 ◽

2000 ◽

Vol 11 (16) ◽

pp. 3277-3281 ◽

Cited By ~ 77

Author(s):

Rafael Chinchilla ◽

Patricia Mazón ◽

Carmen Nájera

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Phase Transfer ◽

Cinchona Alkaloid ◽

Ammonium Salts ◽

Chiral Phase ◽

Phase Transfer Catalysts ◽

Chiral Phase Transfer Catalysts ◽

Polymer Supported

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ChemInform Abstract: Asymmetric Synthesis of α-Amino Acids Using Polymer-Supported Cinchona Alkaloid-Derived Ammonium Salts as Chiral Phase-Transfer Catalysts.

ChemInform ◽

10.1002/chin.200105082 ◽

2001 ◽

Vol 32 (5) ◽

pp. no-no

Author(s):

Rafael Chinchilla ◽

Patricia Mazon ◽

Carmen Najera

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Phase Transfer ◽

Cinchona Alkaloid ◽

Ammonium Salts ◽

Chiral Phase ◽

Phase Transfer Catalysts ◽

Chiral Phase Transfer Catalysts ◽

Polymer Supported

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Syntheses of new dimeric-Cinchona alkaloid as a chiral phase transfer catalysts for the alkylation of Schiff base

Journal of Molecular Catalysis A Chemical ◽

10.1016/j.molcata.2005.06.059 ◽

2005 ◽

Vol 241 (1-2) ◽

pp. 111-117 ◽

Cited By ~ 17

Author(s):

Ayyanar Siva ◽

Eagambaram Murugan

Keyword(s):

Schiff Base ◽

Phase Transfer ◽

Cinchona Alkaloid ◽

Chiral Phase ◽

Phase Transfer Catalysts ◽

Chiral Phase Transfer Catalysts

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Crown Ethers, Taddol, Nobin and Metal(salen) Complexes as Chiral Phase-Transfer Catalysts for Asymmetric Synthesis

Asymmetric Phase Transfer Catalysis ◽

10.1002/9783527622627.ch8 ◽

2008 ◽

pp. 161-187 ◽

Cited By ~ 1

Author(s):

Michael North

Keyword(s):

Asymmetric Synthesis ◽

Crown Ethers ◽

Phase Transfer ◽

Chiral Phase ◽

Phase Transfer Catalysts ◽

Salen Complexes ◽

Chiral Phase Transfer Catalysts

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New trimeric Cinchona alkaloid-based quaternary ammonium salts as efficient chiral phase transfer catalysts for enantioselective synthesis of α-amino acids

Journal of Molecular Catalysis A Chemical ◽

10.1016/j.molcata.2005.11.039 ◽

2006 ◽

Vol 248 (1-2) ◽

pp. 1-9 ◽

Cited By ~ 24

Author(s):

Ayyanar Siva ◽

Eagambaram Murugan

Keyword(s):

Amino Acids ◽

Quaternary Ammonium ◽

Phase Transfer ◽

Quaternary Ammonium Salts ◽

Enantioselective Synthesis ◽

Cinchona Alkaloid ◽

Ammonium Salts ◽

Chiral Phase ◽

Phase Transfer Catalysts ◽

Chiral Phase Transfer Catalysts

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Convenient Preparation of Chiral Phase-Transfer Catalysts with Conformationally Fixed Biphenyl Core for Catalytic Asymmetric Synthesis of α-Alkyl- and α,α-Dialkyl-α-amino Acids: Application to the Short Asymmetric Synthesis of BIRT-377.

ChemInform ◽

10.1002/chin.200741168 ◽

2007 ◽

Vol 38 (41) ◽

Author(s):

Yong-Gang Wang ◽

Mitsuhiro Ueda ◽

Xisheng Wang ◽

Zhenfu Han ◽

Keiji Maruoka

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Phase Transfer ◽

Chiral Phase ◽

Phase Transfer Catalysts ◽

Catalytic Asymmetric Synthesis ◽

Chiral Phase Transfer Catalysts ◽

Catalytic Asymmetric ◽

Convenient Preparation

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Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N-Boc ketimines catalyzed by chiral phase-transfer catalysts

New Journal of Chemistry ◽

10.1039/c7nj04527a ◽

2018 ◽

Vol 42 (3) ◽

pp. 1608-1611 ◽

Cited By ~ 5

Author(s):

Yuxin Liu ◽

Jingdong Wang ◽

Zhonglin Wei ◽

Jungang Cao ◽

Dapeng Liang ◽

...

Keyword(s):

Mannich Reaction ◽

Phase Transfer ◽

Cinchona Alkaloid ◽

Chiral Phase ◽

Phase Transfer Catalysts ◽

Chiral Phase Transfer Catalysts

A series of 3-substituted 3-amino-oxindoles were constructed in excellent yields (96–99%) with high enantioselectivities (up to 95% ee) and diastereoselectivities (up to 95 : 5 dr) catalyzed by Cinchona alkaloid-derived phase-transfer catalysts.

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