The application of HETPHOX ligands to the asymmetric intermolecular heck reaction

被引：23
|
作者：
Kilroy, TG
Cozzi, PG
End, N
Guiry, PJ [1 ]
机构：
[1] Univ Coll Dublin, Ctr Synth & Chem Biol, Conway Inst Biomol & Biomed Res, Dept Chem, Dublin 4, Ireland
[2] Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
[3] Ciba Special Grp Res, CH-4002 Basel, Switzerland
来源：
SYNLETT | 2004年 / 01期
关键词：
P; N ligands; oxazoline; asymmetric catalysis; intermolecular Heck reaction; palladium;
D O I：
10.1055/s-2003-43345
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two new heterocyclic diphenylphosphinooxazolines derived from thiophene and benzothiophene were prepared in moderate to good yield and these, and a range of related HETPHOX ligands, were applied in the intermolecular asymmetric Heck reaction. Phenylation of 2,3-dihydrofuran with the t-butyl-substituted thiophene-oxazoline ligand gave (R)-2-phenyl-2,3-dihydrofuran highly regioselectively with excellent enantioselectivity (91-95% ee) and in good yields (70-97%). In addition, cyclohexenylation of 2,3-dihydrofuran proceeded with enantioselectivities of up to 97% ee in excellent (97%) yields, again with the t-butyl-substituted thiophene-oxazoline ligand proving optimal over a range of reaction conditions investigated.
引用
收藏
页码：106 / 110
页数：5
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