Asymmetric Hydrogenation of Bicyclic Ketones Catalyzed by BINAP/IPHAN-Ru(II) Complex

被引：30

作者：

Arai, Noriyoshi ^{[1
]}

Akashi, Masaya ^{[2
]}

Sugizaki, Satoshi ^{[1
]}

Ooka, Hirohito ^{[1
,2
]}

Inoue, Tsutomu ^{[2
]}

Ohkuma, Takeshi ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Engn, Div Chem Proc Engn, Sapporo, Hokkaido 0608628, Japan

[2] Nippon Soda Co Ltd, Odawara Res Ctr, Odawara, Kanagawa 2500280, Japan

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 15期

基金：

日本科学技术振兴机构; 日本学术振兴会;

关键词：

DYNAMIC KINETIC RESOLUTION; STEREOSELECTIVE HYDROGENATION; WIDE SCOPE; ENANTIOSELECTIVITY; ANTAGONISTS;

D O I：

10.1021/ol101200z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrogenation of 3-quinuclidinone and bicyclo[2.2.2]octan-2-one with a combined catalyst system of RuCl(2)[(S)-binap][(R)-iphan] and t-C(4)H(9)OK in 2-propanol afforded the chiral alcohols in 97-98% ee. 2-Diphenylmethyl-3-quinuclidinone was hydrogenated with the same catalyst to the cis alcohol with perfect diastereo- and enantioselectivity. The reaction of unsymmetrical ketones with a bicyclo[2.2.1] or -[2.2.2] skeleton gave the corresponding alcohols with high stereoselectivity.

引用

页码：3380 / 3383

页数：4

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