Asymmetric synthesis of quaternary α-trifluoromethyl α-amino acids by Ir-catalyzed allylation followed by kinetic resolution

Xi-Shang Sun; Qiu Ou-Yang; Shi-Ming Xu; Xing-Heng Wang; Hai-Yan Tao; Lung Wa Chung; Chun-Jiang Wang

doi:10.1039/d0cc00845a

Asymmetric synthesis of quaternary α-trifluoromethyl α-amino acids by Ir-catalyzed allylation followed by kinetic resolution

Chemical Communications ◽

10.1039/d0cc00845a ◽

2020 ◽

Vol 56 (22) ◽

pp. 3333-3336 ◽

Cited By ~ 5

Author(s):

Xi-Shang Sun ◽

Qiu Ou-Yang ◽

Shi-Ming Xu ◽

Xing-Heng Wang ◽

Hai-Yan Tao ◽

...

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Kinetic Resolution ◽

Asymmetric Allylation ◽

Sequential Reaction

Facile access to quaternary α-trifluoromethyl α-amino acids has been developed. This sequential reaction involves an Ir-catalyzed asymmetric allylation of α-trifluoromethyl aldimine esters followed by an unprecedented kinetic resolution.

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Dynamic Kinetic Resolution for Asymmetric Synthesis of α-Alkyl Amino Acids via Dual-Function Catalysis of Modified Cinchona Alkaloids

Synlett ◽

10.1055/s-2003-41500 ◽

2003 ◽

pp. 1927-1930 ◽

Cited By ~ 2

Author(s):

Li Deng ◽

Jianfeng Hang

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Kinetic Resolution ◽

Cinchona Alkaloids ◽

Dual Function ◽

Dynamic Kinetic Resolution

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Dynamic Kinetic Resolution for Asymmetric Synthesis of L-Noncanonical Amino Acids from D-Ser Using Tryptophan Synthase and Alanine Racemase

European Journal of Organic Chemistry ◽

10.1002/ejoc.201901132 ◽

2019 ◽

Vol 2019 (39) ◽

pp. 6618-6625 ◽

Cited By ~ 5

Author(s):

Jinhai Yu ◽

Jing Li ◽

Xia Gao ◽

Shuiyun Zeng ◽

Hongjuan Zhang ◽

...

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Kinetic Resolution ◽

Alanine Racemase ◽

Tryptophan Synthase ◽

Dynamic Kinetic Resolution ◽

Noncanonical Amino Acids

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Development of a Rapid, Room-Temperature Dynamic Kinetic Resolution for Efficient Asymmetric Synthesis of α-Aryl Amino Acids

Organic Letters ◽

10.1021/ol026660l ◽

2002 ◽

Vol 4 (19) ◽

pp. 3321-3324 ◽

Cited By ~ 52

Author(s):

Jianfeng Hang ◽

Hongming Li ◽

Li Deng

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Room Temperature ◽

Kinetic Resolution ◽

Dynamic Kinetic Resolution ◽

Temperature Dynamic

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ChemInform Abstract: Asymmetric Synthesis of α-Amino Acids via Cinchona Alkaloid-Catalyzed Kinetic Resolution of Urethane-Protected α-Amino Acid N-Carboxyanhydrides.

ChemInform ◽

10.1002/chin.200222174 ◽

2010 ◽

Vol 33 (22) ◽

pp. no-no

Author(s):

Jianfeng Hang ◽

Shi-Kai Tian ◽

Liang Tang ◽

Li Deng

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Asymmetric Synthesis ◽

Kinetic Resolution ◽

Cinchona Alkaloid

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Development of a Rapid Room-Temperature Dynamic Kinetic Resolution for Efficient Asymmetric Synthesis of α-Aryl Amino Acids.

ChemInform ◽

10.1002/chin.200304031 ◽

2003 ◽

Vol 34 (4) ◽

Author(s):

Jianfeng Hang ◽

Hongming Li ◽

Li Deng

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Room Temperature ◽

Kinetic Resolution ◽

Dynamic Kinetic Resolution ◽

Temperature Dynamic

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Asymmetric synthesis of β,γ-unsaturated α-amino acids via efficient kinetic resolution with cinchona alkaloids

Bioorganic & Medicinal Chemistry Letters ◽

10.1016/j.bmcl.2009.03.152 ◽

2009 ◽

Vol 19 (14) ◽

pp. 3856-3858 ◽

Cited By ~ 14

Author(s):

Jianfeng Hang ◽

Li Deng

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Kinetic Resolution ◽

Cinchona Alkaloids

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Dynamic Kinetic Resolution for Asymmetric Synthesis of α-Alkyl Amino Acids via Dual-Function Catalysis of Modified Cinchona Alkaloids.

ChemInform ◽

10.1002/chin.200407167 ◽

2004 ◽

Vol 35 (7) ◽

Author(s):

Jianfeng Hang ◽

Li Deng

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Kinetic Resolution ◽

Cinchona Alkaloids ◽

Dual Function ◽

Dynamic Kinetic Resolution

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Dynamic Kinetic Resolution in the Asymmetric Synthesis of β-Amino Acids by Organocatalytic Reduction of Enamines with Trichlorosilane

Chemistry - A European Journal ◽

10.1002/chem.200801244 ◽

2008 ◽

Vol 14 (27) ◽

pp. 8082-8085 ◽

Cited By ~ 77

Author(s):

Andrei V. Malkov ◽

Sigitas Stončius ◽

Kvetoslava Vranková ◽

Matthias Arndt ◽

Pavel Kočovský

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Kinetic Resolution ◽

Dynamic Kinetic Resolution

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Asymmetric synthesis of β-amino acids: Dynamic kinetic resolution utilizing 2-oxoimidazolidine-4-carboxylate as a chiral auxiliary

Peptide Science — Present and Future ◽

10.1007/0-306-46864-6_256 ◽

2006 ◽

pp. 752-754

Author(s):

K. Nunami ◽

A. Kubo ◽

H. Kubota ◽

M. Takahashi

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Kinetic Resolution ◽

Chiral Auxiliary ◽

Dynamic Kinetic Resolution

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Asymmetric Synthesis of α-Amino Acids via Cinchona Alkaloid-Catalyzed Kinetic Resolution of Urethane-Protected α-Amino AcidN-Carboxyanhydrides

Journal of the American Chemical Society ◽

10.1021/ja011936q ◽

2001 ◽

Vol 123 (50) ◽

pp. 12696-12697 ◽

Cited By ~ 44

Author(s):

Jianfeng Hang ◽

Shi-Kai Tian ◽

Liang Tang ◽

Li Deng

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Kinetic Resolution ◽

Cinchona Alkaloid

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