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
收藏
页码：204 / 207
页数：4
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