Regioselective Semihydrogenation of Dienes

被引：12

作者：

Graham, Thomas J. A. ^{[1
]}

Poole, Thomas H. ^{[1
]}

Reese, Charles N. ^{[1
]}

Goess, Brian C. ^{[1
]}

机构：

[1] Furman Univ, Dept Chem, Greenville, SC 29613 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 10期

关键词：

SELECTIVE REDUCING AGENT; ALPHA; BETA-UNSATURATED ALDEHYDES; FUNCTIONAL-GROUPS; EFFICIENT METHOD; HYDROGENATION; HYDROBORATION; 9-BORABICYCLO<3.3.1>NONANE; ORGANOBORANES; REDUCTIONS; CONVERSION;

D O I：

10.1021/jo200262r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot, three-step strategy for the regioselective semihydrogenation of dienes is described. This procedure uses 9-BBN-H as a temporary protective group for alkenes. Yields range from 55% to 95%, and the reaction is tolerant of a variety of common functional groups. Additionally, the final elimination step of the sequence can be replaced with a peroxide-mediated alkylborane oxidation, generating regioselectively semihydrogenated product alcohols.

引用

页码：4132 / 4138

页数：7

共 30 条

[11]

Freifelder M., 1978, Catalytic Hydrogenation in Organic Synthesis

[12]

Kluwer A. M., 2007, HDB HOMOGENEOUS HYDR, P375

[13] 9-BORABICYCLO[3.3.1]NONANE AS A HIGHLY SELECTIVE REDUCING AGENT FOR FACILE CONVERSION OF ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES TO CORRESPONDING ALLYLIC ALCOHOLS IN PRESENCE OF OTHER FUNCTIONAL GROUPS [J].