CATALYTIC ASYMMETRIC ARYLATION OF OLEFINS

被引：107

作者：

HAYASHI, T ^{[1
]}

KUBO, A ^{[1
]}

OZAWA, F ^{[1
]}

机构：

[1] HOKKAIDO UNIV,GRAD SCH PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN

来源：

PURE AND APPLIED CHEMISTRY | 1992年 / 64卷 / 03期

关键词：

D O I：

10.1351/pac199264030421

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic asymmetric arylation of 2,3-dihydrofuran with aryl triflate (1) in benzene at 40-degrees-C in the presence of a base and a palladium catalyst, generated in situ from Pd(OAc)2 and (R)-BINAP, gave optically active (R)-2-aryl-2,3-dihydrofuran (2) and a small amount of (S)-2-aryl-2,5-dihydrofuran (3). The relative ratio of 2 to 3 and the enantiomeric purities of the products were dependent upon the base employed. 1,8-Bis(dimethylamino)naphthalene (proton sponge) as a highly basic and sterically demanding amine gave major product (R)-2 in extremely high enantioselectivity (> 96-87% ee) for a variety of aryl triflates. The mechanism of this novel catalytic asymmetric reaction is discussed in detail.

引用

页码：421 / 427

页数：7

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