Stereoselective formation of carbon-carbon bonds via SN2-displacement:: Synthesis of substituted cycloalkyl[b]indoles

被引：51

作者：

Hillier, MC ^{[1
]}

Marcoux, JF ^{[1
]}

Zhao, DL ^{[1
]}

Grabowski, EJJ ^{[1
]}

McKeown, AE ^{[1
]}

Tillyer, RD ^{[1
]}

机构：

[1] Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 21期

关键词：

D O I：

10.1021/jo051146p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general asymmetric synthesis of substituted cycloalkyl[b]indoles has been accomplished. The key features of this approach are (1) the utilization of a Japp-Klingemann condensation/Fischer cyclization to prepare cycloalkyl[b]indolones, (2) the asymmetric borane reduction of these heterocyclic ketones with (S)-OAB to obtain enantiomerically pure alcohols, and (3) the stereoselective S(N)2-displacement of these indole alcohol substrates with a carbon nucleophile under Mitsunobu conditions to set the C-1 or C-3 tertiary carbon stereocenter. The use of trimethylphosphine (PMe3) and bis(2,2,2-trichloroethyl) azodicarboxylate (TCEAD) was found to have an effect on the Mitsunobu dehydrative alkylation.

引用

页码：8385 / 8394

页数：10

共 43 条

[1]

ASHWELL MA, 1994, Patent No. 9408983

[2]

Asselin A. A., 1977, U.S. Patent, Patent No. 4057599

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