Lewis acid promoted hetero [2+2] cycloaddition reactions of aldehydes with 10-propynyl-9(10H)-acridone.: A highly stereoselective synthesis of acrylic acid derivatives and 1,3-dienes using an electron deficient variant of ynamine

被引：78

作者：

Hsung, RP ^{[1
]}

Zificsak, CA ^{[1
]}

Wei, LL ^{[1
]}

Douglas, CJ ^{[1
]}

Xiong, H ^{[1
]}

Mulder, JA ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 08期

关键词：

D O I：

10.1021/ol990211c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Reactivities of 10 propynyl-9(10H)-acridone toward various aldehydes in BF3. Et2O-promoted hetero [2 + 2] cycloaddition reactions are described here. This electron deficient variant of ynamine is more stable and easier to handle than most ynamines but possesses comparable reactivity. These reactions lead to a highly stereoselective synthesis of trisubstituted alkenes. A mechanistic model based on the stereochemical assignment is also described here, 10-Propynyl-9(10H)-acridone is also reactive toward ag-unsaturated aldehydes and ketones. It provides hetero [2 + 2] products in reactions with alpha,beta-unsaturated aldehydes but gives only the inverse demand [4 + 2] cycloadduct in a reaction with methyl vinyl ketone.

引用

页码：1237 / 1240

页数：4

共 27 条

[1] 3-(4-IODOMETHYL-2-OXO-1-AZETIDINYL)PROPYNOIC ACID TERT-BUTYL ESTER - A NEW BETA-LACTAM DERIVATIVE, SYNTHESIS OF AN YNAMIDE BY REACTION OF 4-IODOMETHYLAZETIDIN-2-ONE WITH THE TERT-BUTYL ESTER OF PROPIOLIC ACID IN THE PRESENCE OF COPPER(I) [J].