Asymmetric addition of allylic stannanes to aldehydes catalyzed by BINAP•Ag(I) complex

被引:40
作者
Yanagisawa, A [1 ]
Nakashima, H [1 ]
Nakatsuka, Y [1 ]
Ishiba, A [1 ]
Yamamoto, H [1 ]
机构
[1] Nagoya Univ, CREST, Japan Sci & Technol Corp, JST,Grad Sch Engn, Nagoya, Aichi 4648603, Japan
关键词
D O I
10.1246/bcsj.74.1129
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic asymmetric allylation of aldehydes with allylic trialkylstannanes was achieved with BINAP . AgOTf complex as catalyst. The chiral silver(I) catalyst was readily prepared by stirring an equimolar mixture of BINAP and silver(I) triflate in THF at room temperature. The allylation of a variety of aromatic and alpha,beta -unsaturated aldehydes resulted in high yields and remarkable enantioselectivities. Addition of gamma -substituted allylstannanes such as 2-butenyltributylstannane and trialkyl-2,4-pentadienylstannanes exclusively gave gamma -adducts. High anti-selectivity was also obtained in the reaction with 2-butenyltributylstannane, irrespective of the configuration at the double bond.
引用
收藏
页码:1129 / 1137
页数:9
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