Organocatalytic asymmetric hydrophosphination of α,β-Unsaturated aldehydes

被引:149
作者
Carlone, Armando [1 ]
Bartoli, Giuseppe [1 ]
Bosco, Marcella [1 ]
Sambri, Letizia [1 ]
Melchiorre, Paolo [1 ]
机构
[1] Univ Bologna, Dept Organ Chem A Mangini Alma Mater Studiorum, I-40136 Bologna, Italy
关键词
aldehydes; asymmetric synthesis; conjugate addition; organocatalysis; phosphanes;
D O I
10.1002/anie.200700754
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Getting round the (periodic) table: A highly chemo- and enantioselective conjugate addition of diphenylphosphine to α,β-unsaturated aldehydes in the presence of a chiral secondary amine C provides a direct route to chiral β-phosphino aldehyde intermediates (see scheme, TMS = trimethylsilyl). The synthetic utility of the strategy was exemplified in a rapid one-pot (two-step) synthesis of highly enantioenriched 3-amino-phosphines. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4504 / 4506
页数:3
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