One-Pot Formation of Chiral Polysubstituted 3,4-Dihydropyrans via a Novel Organocatalytic Domino Sequence Involving Alkynal Self-Condensation

被引：29

作者：

Dong, Li-Jin ^{[1
,2
]}

Fan, Tian-Tian ^{[1
,2
]}

Wang, Chao ^{[1
]}

Sun, Jian ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Biol, Nat Prod Res Ctr, Chengdu 610041, Peoples R China

[2] Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 01期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTIONS; ASYMMETRIC-SYNTHESIS; CASCADE REACTIONS; TANDEM REACTIONS; ACCESS; 4-ISOXAZOLINES; 4H-CHROMENES; CATALYSIS; NITRONES;

D O I：

10.1021/ol3032285

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The self-condensation of alkynals was for the first time implemented under mild organocatalytic conditions and was successfully linked with a domino organocatalytic inverse-electron-demand oza-Diels-Alder reaction, which led to the development of a facile one-pot method to produce a wide variety of polysubstituted chiral 3,4-dihydropyrans with good to high yields and diastereoselectivities and high enantioselectivities. The unprecedented alkynal self-condensation was revealed to pass through secondary amine-catalyzed C-C triple bond hydration and subsequent aldol condensation.

引用

页码：204 / 207

页数：4

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