An Enantioselective Approach to the Preparation of Chiral Sulfones by Ir-Catalyzed Asymmetric Hydrogenation

被引：81

作者：

Peters, Byron K. ^{[1
]}

Zhou, Taigang ^{[1
]}

Rujirawanich, Janjira ^{[2
]}

Cadu, Alban ^{[2
]}

Singh, Thishana ^{[1
,2
]}

Rabten, Wangchuk ^{[1
]}

Kerdphon, Sutthichat ^{[1
]}

Andersson, Pher G. ^{[1
]}

机构：

[1] Univ Stockholm, Dept Organ Chem, S-10691 Stockholm, Sweden

[2] Uppsala Univ, Dept Chem BMC, S-75123 Uppsala, Sweden

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 47期

基金：

瑞典研究理事会; 新加坡国家研究基金会;

关键词：

INTRAMOLECULAR CYCLOPROPANATION; 1,3-DIPOLAR CYCLOADDITION; IRIDIUM CATALYSTS; OXAZOLINE LIGANDS; GENERAL-SYNTHESIS; LEWIS-ACID; ALPHA; OLEFINS; COORDINATION; CONSTRUCTION;

D O I：

10.1021/ja5079877

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Several chiral sulfonyl compounds were prepared using the iridium catalyzed asymmetric hydrogenation reaction. Vinylic, allylic and homoallylic sulfone substitutions were investigated, and high enantioselectivity is maintained regardless of the location of the olefin with respect to the sulfone. Impressive stereoselectivity was obtained for dialkyl substitutions, which typically are challenging substrates in the hydrogenation. As expected, the more bulky Z-substrates were hydrogenated slower than the corresponding E isomers, and in slightly lower enantioselectivity.

引用

页码：16557 / 16562

页数：6

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