Scale-Up of an Enantioselective Overman Rearrangement for an Asymmetric Synthesis of a Glycine Transporter 1 Inhibitor

被引：9

作者：

Chandramouli, Sithamalli V. ^{[1
]}

Ayers, Timothy A. ^{[1
]}

Wu, Xiao-Dong ^{[1
]}

Tran, Loc T. ^{[1
]}

Peers, James H. ^{[1
]}

Disanto, Rocco ^{[1
]}

Roberts, Frederick ^{[1
]}

Kumar, Narendra ^{[1
]}

Jiang, Ying ^{[1
]}

Choy, Nakyen ^{[1
]}

Pemberton, Clive ^{[1
]}

Powers, Matthew R. ^{[1
]}

Gardetto, Anthony J. ^{[1
]}

D'Netto, Geoffrey A. ^{[1
]}

Chen, Xuemin ^{[1
]}

Gamboa, Juan ^{[1
]}

Duc Ngo ^{[1
]}

Copeland, Warren ^{[1
]}

Rudisill, Duane E. ^{[1
]}

Bridge, Andrew W. ^{[1
]}

Vanasse, Benoit J. ^{[1
]}

Lythgoe, David J. ^{[1
]}

机构：

[1] Sanofi, Mol Innovat Therapeut, Bridgewater, NJ 08807 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2012年 / 16卷 / 03期

关键词：

ALLYLIC AMINES; HYDROGENATION; CATALYSIS; CHEMISTRY; RHODIUM; FACILE;

D O I：

10.1021/op200378r

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An enantioselective Overman 3,3-sigmatropic rearrangement on a quinuclidine skeleton was developed for the pilot-plant synthesis of a glycine transporter 1 inhibitor. The first stereocenter was produced by a Ru-catalyzed asymmetric transfer hydrogenation process followed by chirality transfer using the Overman rearrangement. The second stereocenter was generated by a diastereoselective hydrogenation reaction.

引用

页码：484 / 494

页数：11

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