Enantioselective [4+2]-Annulation of Oxadienes and Allenones Catalyzed by an Amino Acid Derived Phosphine: Synthesis of Functionalized Dihydropyrans

被引：51
|
作者：
Ni, Huanzhen [1 ,2 ]
Yao, Weijun [2 ]
Waheed, Abdul [3 ]
Ullah, Nisar [3 ]
Lu, Yixin [1 ,2 ]
机构：
[1] Natl Univ Singapore, Ctr Life Sci CeLS, Grad Sch Integrat Sci & Engn NGS, 05-01,28 Med Dr, Singapore 117456, Singapore
[2] Natl Univ Singapore, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore
[3] King Fahd Univ Petr & Minerals, Dept Chem, Dhahran 31261, Saudi Arabia
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 09期
关键词：
MORITA-BAYLIS-HILLMAN; ASYMMETRIC 3+2 CYCLOADDITION; ELECTRON-DEFICIENT OLEFINS; DIPEPTIDE-BASED PHOSPHINES; N-ACYL AMINOPHOSPHINES; 4+2 ANNULATION; MICHAEL ADDITION; NATURAL-PRODUCTS; GAMMA-ADDITION; FUSED TETRAHYDROPYRIDINES;
D O I：
10.1021/acs.orglett.6b00760
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An enantioselective [4 + 2]-annulation process between cyano-activated oxadienes and allenones is developed. An L-valine-derived phosphine was efficient in catalyzing the reaction, and a wide range of highly functionalized dihydropyrans were prepared in high yields and with excellent enantioselectivities.
引用
收藏
页码：2138 / 2141
页数：4
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