Asymmetric synthesis of 5-arylcyclohexenones by rhodium(I)-catalyzed conjugate arylation of racemic 5-(trimethylsilyl)cyclohexenone with arylboronic acids

被引：28

作者：

Chen, O ^{[1
]}

Kuriyama, M ^{[1
]}

Soeta, T ^{[1
]}

Hao, XY ^{[1
]}

Yamada, KI ^{[1
]}

Tomioka, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 20期

关键词：

D O I：

10.1021/ol051704m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic asymmetric conjugate arylation of racemic 5-(trimethylsilyl)cyclohex-2-enone with arylboronic acids was catalyzed by 3 mol % chiral amidophosphane- or BINAP-Rh(l) in dioxane-water (10:1) to afford trans- and cis-3-aryl-5-(trimethylsilyl)cyclohexanones in high enantioselectivity. Dehydrosilylation of the product mixture with cupric chloride in DMF gave 5-arylcyclohex-2-enones with up to 93% ee in good yield. Enantiofacial selectivity with chiral phosphane-Rh(l) exceeds the trans-diastereoselectivity that is maintained in the achiral or racemic phosphane-Rh(l)-catalyzed conjugate arylation of 5-(trimethylsilyl)cyclohexenone.

引用

页码：4439 / 4441

页数：3

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