Chiral 1,3,2-Diazaphospholenes as Catalytic Molecular Hydrides for Enantioselective Conjugate Reductions

被引:52
作者
Miaskiewicz, Solene [1 ]
Reed, John H. [1 ]
Donets, Pavel A. [1 ]
Oliveira, Caio C. [1 ]
Cramer, Nicolai [1 ]
机构
[1] EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, BCH 4305, CH-1015 Lausanne, Switzerland
基金
瑞士国家科学基金会;
关键词
asymmetric catalysis; diazaphospholenes; organocatalysis; phosphorus; reduction; N-HETEROCYCLIC PHOSPHINES; ASYMMETRIC HYDROGENATION; CARBENE LIGANDS; HYDROBORATION; ESTERS; BOND;
D O I
10.1002/anie.201801300
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Secondary 1,3,2-diazaphospholenes have a polarized P-H bond and are emerging as molecular hydrides. Herein, a class of chiral, conformationally restricted methoxy-1,3,2-diazaphospholene catalysts is reported. We demonstrate their catalytic potential in asymmetric 1,4-reductions of ,-unsaturated carbonyl derivatives, including enones, acyl pyrroles, and amides, which proceeded in enantioselectivities of up to 95.5:4.5 e.r.
引用
收藏
页码:4039 / 4042
页数:4
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