Asymmetric Synthesis of Tetrasubstituted Cyclic Amines via Aza-Henry Reaction using Cinchona Alkaloid Sulfonamide/Zinc(II) Catalysts

Chemical Communications ◽

10.1039/d1cc06492d ◽

2022 ◽

Author(s):

Naoki Yasukawa ◽

Ami Yamanoue ◽

Tsunayoshi Takehara ◽

Takeyuki Suzuki ◽

Shuichi Nakamura

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Cinchona Alkaloid ◽

Henry Reaction ◽

Cyclic Amines ◽

Cyclic Amino Acids

The first enantioselective aza-Henry reaction of non-activated cyclic iminoesters, derived from cyclic amino acids, has been developed. Good yields and enantioselectivities were observed for the reaction using our original cinchona...

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Asymmetric synthesis of cyclic β-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis

Tetrahedron ◽

10.1016/s0040-4020(03)00411-3 ◽

2003 ◽

Vol 59 (18) ◽

pp. 3253-3265 ◽

Cited By ~ 73

Author(s):

Ann M Chippindale ◽

Stephen G Davies ◽

Keiji Iwamoto ◽

Richard M Parkin ◽

Christian A.P Smethurst ◽

...

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Conjugate Addition ◽

Ring Closing Metathesis ◽

Cyclic Amines

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Asymmetric Synthesis of Functionalized Aza-Cyclic Amino Acids with Quaternary Stereocenters by a Phase-Transfer-Catalyzed Alkylation Strategy

Organic Letters ◽

10.1021/ol047921p ◽

2005 ◽

Vol 7 (2) ◽

pp. 191-193 ◽

Cited By ~ 27

Author(s):

Takashi Ooi ◽

Takashi Miki ◽

Keiji Maruoka

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Phase Transfer ◽

Quaternary Stereocenters ◽

Cyclic Amino Acids

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ChemInform Abstract: Electrochemical Deallylation of α-Allyl Cyclic Amines and Synthesis of Optically Active Quaternary Cyclic Amino Acids.

ChemInform ◽

10.1002/chin.201037022 ◽

2010 ◽

Vol 41 (37) ◽

pp. no-no

Author(s):

Peter G. Kirira ◽

Masami Kuriyama ◽

Osamu Onomura

Keyword(s):

Amino Acids ◽

Optically Active ◽

Cyclic Amines ◽

Cyclic Amino Acids

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Catalytic asymmetric synthesis of cyclic amino acids and alkaloid derivatives: application to (+)-dihydropinidine and Selfotel synthesis

Chemical Science ◽

10.1039/c0sc00250j ◽

2010 ◽

Vol 1 (4) ◽

pp. 499 ◽

Cited By ~ 13

Author(s):

Taichi Kano ◽

Takeshi Kumano ◽

Ryu Sakamoto ◽

Keiji Maruoka

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Catalytic Asymmetric Synthesis ◽

Catalytic Asymmetric ◽

Cyclic Amino Acids

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Asymmetric Synthesis of Cyclic β-Amino Acids and Cyclic Amines via Sequential Diastereoselective Conjugate Addition and Ring Closing Metathesis.

ChemInform ◽

10.1002/chin.200334018 ◽

2003 ◽

Vol 34 (34) ◽

Author(s):

Ann M. Chippindale ◽

Stephen G. Davies ◽

Keiji Iwamoto ◽

Richard M. Parkin ◽

Christian A. P. Smethurst ◽

...

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Conjugate Addition ◽

Ring Closing Metathesis ◽

Cyclic Amines

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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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ChemInform Abstract: Asymmetric Synthesis of Chiral Cyclic Amino Acids by Diels-Alder Reactions of (2S)- and (2R)-4-Methyleneoxazolidin-5-ones.

ChemInform ◽

10.1002/chin.199320055 ◽

2010 ◽

Vol 24 (20) ◽

pp. no-no

Author(s):

S. G. PYNE ◽

B. DIKIC ◽

P. A. GORDON ◽

B. W. SKELTON ◽

A. H. WHITE

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Diels Alder ◽

Cyclic Amino Acids

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Asymmetric\ Synthesis of Chiral Cyclic Amino Acids by Diels-Alder Reactions of (2S)- and (2R)-4-Methyleneoxazolidin-5-ones

Australian Journal of Chemistry ◽

10.1071/ch9930073 ◽

1993 ◽

Vol 46 (1) ◽

pp. 73 ◽

Cited By ~ 20

Author(s):

SG Pyne ◽

B Dikic ◽

PA Gordon ◽

BW Skelton ◽

AH White

Keyword(s):

Amino Acids ◽

Carboxylic Acid ◽

Single Crystal ◽

Asymmetric Synthesis ◽

Enantiomeric Purity ◽

Diels Alder ◽

X Ray ◽

Cyclic Dienes ◽

Ray Methods ◽

Cyclic Amino Acids

The synthesis of chiral (2S)- and (2R)-4-methyleneoxazolidin-5-ones, in high enantiomeric purity from (S)-S- methylcysteine, and their highly exo-selective Diels -Alder reactions with cyclic dienes are described. (1R,2S,4S)-2-Aminobicyclo[2.2.1]heptane-2-carboxylic acid has been prepared in 92% e.e. by these methods. A number of the products have been characterized by single-crystal X-ray methods, and their structure systematics examined.

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