Highly Enantioselective Oxazaborolidine-Catalyzed Reduction of 1,3-Dicarbonyl Compounds: Role of the Additive Diethylaniline

被引：12

作者：

Chein, Rong-Jie ^{[1
]}

Yeung, Ying-Yeung ^{[1
]}

Corey, E. J. ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 07期

关键词：

D O I：

10.1021/ol900258f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxazaborolidine-catalyzed reduction of 2,2-disubstituted cycloalkan-1,3-diones or hindered 2,2-disubstituted cyclic ketones using catecholborane as reductant proceeds with greater enantioselectivity when N,N-diethylaniline is added. It has now been shown that the effect of this additive is to catalyze the conversion of a harmful minor impurity in catalyst preparations to the active catalyst.

引用

页码：1611 / 1614

页数：4

共 5 条

[1]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO

[2]

2-Z

[3] AN ASYMMETRIC-SYNTHESIS OF MK-0417 - OBSERVATIONS ON OXAZABOROLIDINE-CATALYZED REDUCTIONS [J].

JONES, TK ;

MOHAN, JJ ;

XAVIER, LC ;

BLACKLOCK, TJ ;

MATHRE, DJ ;

SOHAR, P ;

JONES, ETT ;

REAMER, RA ;

ROBERTS, FE ;

GRABOWSKI, EJJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :763-769

[4] HYDROBORATION WITH BORON HALIDES AND TRIALKYLSILANES [J].

SOUNDARARAJAN, R ;

MATTESON, DS .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) :2274-2275

[5] Conversion of Torgov's synthesis of estrone into a highly enantioselective and efficient process [J].

Yeung, Ying-Yeung ;

Chein, Rong-Jie ;

Corey, E. J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (34) :10346-+

← 1 →