Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with sulfur nucleophiles

被引：93

作者：

Leong, P ^{[1
]}

Lautens, M ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 06期

关键词：

D O I：

10.1021/jo035730e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 2-sulfanyl-1,2-dihydro-naphthalen-1-ols is described. This methodology is based on rhodium catalysis and enables various thiols to undergo an asymmetric S(N)2' ring opening of oxabenzonorbornadiene. Under the reaction conditions ([Rh(COD)Cl](2) (2.5 mol %), (S)-(R)-PPF-(PBu2)-Bu-t (6 mol %) AgOTf (7 mol %), NH4I (1.7 equiv), galvinoxyl (5 mol %) THF, 85 degreesC, aryl- and alkyl-sulfide adducts are obtained in good to excellent yield and in high enantiomeric excess (> 90% ee).

引用

页码：2194 / 2196

页数：3

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