Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor

被引：42

作者：

Davis, Tyler A.

Danneman, Michael W.

Johnston, Jeffrey N. ^{[1
]}

机构：

[1] Vanderbilt Univ, Dept Chem, Nashville, TN 37235 USA

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 45期

关键词：

AZA-HENRY REACTION; ENANTIOSELECTIVE SYNTHESIS; NITRO-GROUP; THIOUREA; HYDROGEN; ORGANOCATALYST; REPLACEMENT; ACTIVATION; REACTIVITY; PROGRESS;

D O I：

10.1039/c2cc32225k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first enantioselective synthesis of a potent GlyT1 inhibitor is described. A 3-nitroazetidine donor is used in an enantioselective aza-Henry reaction catalyzed by a bis(amidine)-triflic acid salt organocatalyst, delivering the key intermediate with 92% ee. This adduct is reductively denitrated and converted to the target through a short sequence, thereby allowing assignment of the absolute configuration of the more potent enantiomer.

引用

收藏

页码：5578 / 5580

页数：3

相关论文

共 38 条

[1] Recent progress in chiral Bronsted acid catalysis [J].

Akiyama, Takahiko ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010

[2] Novel syntheses of azetidines and azetidinones [J].

Brandi, Alberto ;

Cicchi, Stefano ;

Cordero, Franca M. .

CHEMICAL REVIEWS, 2008, 108 (09) :3988-4035

[3] Oxazoline-thiourea as a bifunctional organocatalyst: Enantioselective aza-Henry reactions [J].

Chang, Yu-wei ;

Yang, Jing-jun ;

Dang, Jin-ning ;

Xue, Yue-xia .

SYNLETT, 2007, (14) :2283-2285

[4] A bench-stable homodinuclear Ni2-chiff base complex for catalytic asymmetric synthesis of α-tetrasubstituted anti-α,β-diamino acid surrogates [J].

Chen, Zhihua ;

Morimoto, Hiroyuki ;

Matsunaga, Shigeki ;

Shibasaki, Masakatsu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (07) :2170-+

[5] Preparation of H,(4) PyrrolidineQuin-BAM (PBAM) [J].

Davis, Tyler A. ;

Dobish, Mark C. ;

Schwieter, Kenneth E. ;

Chun, Aspen C. ;

Johnston, Jeffrey N. ;

Goldberg, Alexander F. G. ;

Stoltz, Brian M. .

ORGANIC SYNTHESES, 2012, 89 :380-393

[6] Catalytic, enantioselective synthesis of stilbene cis-diamines: A concise preparation of (-)-Nutlin-3, a potent p53/MDM2 inhibitor [J].

Davis, Tyler A. ;

Johnston, Jeffrey N. .

CHEMICAL SCIENCE, 2011, 2 (06) :1076-1079

[7] Bifunctional Asymmetric Catalysis: Amplification of Bronsted Basicity Can Orthogonally Increase the Reactivity of a Chiral Bronsted Acid [J].

Davis, Tyler A. ;

Wilt, Jeremy C. ;

Johnston, Jeffrey N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) :2880-+

[8] Chiral Bronsted Base-Promoted Nitroalkane Alkylation: Enantioselective Synthesis of sec-Alkyl-3-Substituted Indoles [J].

Dobish, Mark C. ;

Johnston, Jeffrey N. .

ORGANIC LETTERS, 2010, 12 (24) :5744-5747

[9] Asymmetric aza-henry reaction under phase transfer catalysis:: An experimental and theoretical study [J].

Gomez-Bengoa, Enrique ;

Linden, Anthony ;

Lopez, Rosa ;

Mugica-Mendiola, Idoia ;

Oiarbide, Mike ;

Palomo, Claudio .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (25) :7955-7966

[10] Discovery of Bifunctional Thiourea/Secondary-Amine Organocatalysts for the Highly Stereoselective Nitro-Mannich Reaction of α-Substituted Nitroacetates [J].

Han, Bo ;

Liu, Qing-Ping ;

Li, Rui ;

Tian, Xu ;

Xiong, Xiao-Feng ;

Deng, Jin-Gen ;

Chen, Ying-Chun .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (27) :8094-8097

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