Lewis Acid-Promoted Enantioselective Dearomative Spirocyclizations of Allenes

被引：7

作者：

Tcyrulnikov, Sergei ^{[1
]}

Curto, John M. ^{[1
,2
]}

Gilmartin, Philip H. ^{[1
]}

Kozlowski, Marisa C. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

[2] Pfizer Inc, Eastern Point Rd, Groton, CT 06340 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 19期

基金：

美国国家卫生研究院;

关键词：

HIGH-THROUGHPUT EXPERIMENTATION; COMPLEXES; EPOXIDES;

D O I：

10.1021/acs.joc.8b01565

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral oxazaborolidine combined with SnCl4 has been found to promote the dearomative spirocyclization of electron-rich benzyl allenyl ketones. The reaction outcome is sensitive to the nature of activating acid, which was rationalized using hard-soft acid-base (HSAB) theory. The spirocyclic product was obtained with up to 72% ee, which is the best result reported to date for these substrates. The formation of cross-conjugated or conjugated products is readily controlled by changing the oxygen protecting groups.

引用

收藏

页码：12207 / 12212

页数：6

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