Effects of catalyst activation and ligand steric properties on the enantioselective allylation of amines and phenoxides

被引：112

作者：

Leitner, A ^{[1
]}

Shu, CT ^{[1
]}

Hartwig, JF ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 06期

关键词：

D O I：

10.1021/ol050029d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The yields, enantioselectivities, and regioselectivities of the reactions of amines and phenoxides with allylic carbonates in the presence of a metallacyclic iridium catalyst were compared. These data show that both preactivation of the catalyst and the size of the ligand affect the yield, enantioselectivity, and regioselectivity. With the activated catalyst containing a bis-naphthethylamino group, the allylic amination and etherification of a broad range of allylic carbonates occurred in high yields and with high regioselectivities and enantioselectivities.

引用

页码：1093 / 1096

页数：4

共 36 条

[1]

ACEMOGLU L, 2002, HDB ORGANOPALLADIUM, V2, P1945

[2]

Bartels B, 2003, EUR J ORG CHEM, V2003, P1097

[3]

Bartels B, 2002, EUR J INORG CHEM, P2569

[4] Ir-catalysed allylic substitution: mechanistic aspects and asymmetric synthesis with phosphorus amidites as ligands [J].