Unique Reactivity of anti- and syn-Acetoxypyranones en Route to Oxidopyrylium Intermediates Leading to a Cascade Process

被引：17

作者：

Woodall, Erica L. ^{[1
]}

Simanis, Justin A. ^{[1
]}

Hamaker, Christopher G. ^{[1
]}

Goodell, John R. ^{[1
]}

Mitchell, T. Andrew ^{[1
]}

机构：

[1] Illinois State Univ, Dept Chem, Normal, IL 61790 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 13期

基金：

美国国家科学基金会;

关键词：

ORGANIC-SYNTHESIS; CROSS-METATHESIS; DOMINO REACTIONS; CYCLOADDITION; EXTENSIONS; CATALYSTS;

D O I：

10.1021/ol4012986

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unique reactivity of anti- and syn-acetoxypyranones was observed in oxidopyrylium-alkene [5 + 2] cycloadditions. The subtle interplay between the corresponding acetoxypyranone conformation and steric bulk of tertiary amine bases causes syn-acetoxypyranones to undergo [5 + 2] cycloaddition appreciably faster than anti-acetoxypyranones. Additionally, the efficiency of a cascade process that afforded a novel tetracyclic lactol was determined to be dependent on the relative stereochemistry of each diastereomer, the amine base utilized, and the addition of water.

引用

页码：3270 / 3273

页数：4