Lewis acid-promoted reactions of 3-methoxy-N-(benzenesulfonyl)-1,4-benzoquinone monoimine with propenylbenzenes

被引：14

作者：

Engler, TA ^{[1
]}

Scheibe, CM

机构：

[1] Eli Lilly & Co, Lilly Corp Ctr, Indianapolis, IN 46285 USA

[2] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 18期

关键词：

D O I：

10.1021/jo980502j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

BF3 . OEt2-promoted reactions of 4-N-(benzenesulfonyl)-3-methoxy-1,4-benzoquinone monoimine (5) with (E)-propenylbenzenes bearing strong electron-donating groups on their aromaric rings produce 2-aryl-6-methoxy-3-methyl-5-[N-(benzenesulfonyl)amino]-2,3 -diydrobenzofurans (6). With neutral propenylbenzenes, either the dihydrobenzofurans, bicyclo[3.2.1]octenediones 17, or products of tandem cycloaddition (7-9) are formed depending upon reaction conditions. In the latter, molecules with seven to eight asymmetric centers are formed in a single reaction from achiral starting materials. Thus, these seemingly simple reactions yield products of remarkable complexity, and with a high degree of stereoselectivity.

引用

页码：6247 / 6253

页数：7

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