Asymmetric diene cyclization/hydrosilylation/oxidation employing 1-tert-butyl-3,3-dimethyl-1,1-diphenyldisiloxane

被引:16
作者
Pei, T [1 ]
Widenhoefer, RA [1 ]
机构
[1] Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(00)01321-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A 1:1 mixture of (N-N)Pd(Me)Cl [N-N = (R)-(+)-4-isopropyl-2-(2-pyridinyl)-2-oxazoline] (1) and NaBAr4 [Ar = 3,5-C6H3(CF3)(2)] catalyzed the asymmetric cyclization/hydrosilylation of functionalized 1,6-dienes with 1-tert-butyl-3,3-dimethyl-1,1-diphenyldisiloxane at -20 degrees C to form silylated cyclopentanes in good yield with up to 95% ee. These silylated carbocycles underwent oxidative cleavage of the C-Si bond with H2O2 at room temperature to form the corresponding alcohols. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7597 / 7600
页数:4
相关论文
共 8 条
[1]   The oxidation of the carbon-silicon bond [J].
Jones, GR ;
Landais, Y .
TETRAHEDRON, 1996, 52 (22) :7599-7662
[2]   Use of pentamethyldisiloxane in the palladium-catalyzed cyclization/hydrosilylation of functionalized dienes [J].
Pei, T ;
Widenhoefer, RA .
ORGANIC LETTERS, 2000, 2 (10) :1469-1471
[3]   Enantioselective diene cyclization/hydrosilylation catalyzed by optically active palladium bisoxazoline and pyridine-oxazoline complexes [J].
Perch, NS ;
Pei, T ;
Widenhoefer, RA .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (12) :3836-3845
[4]   Asymmetric cyclization/hydrosilylation of functionalized 1,6-dienes catalyzed by enantiomerically pure palladium pyridine-oxazoline complexes [J].
Perch, NS ;
Widenhoefer, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (29) :6960-6961
[5]   Cyclization/hydrosilylation of functionalized 1,7-dienes to form substituted six-membered carbocycles. [J].
Stengone, CN ;
Widenhoefer, RA .
TETRAHEDRON LETTERS, 1999, 40 (08) :1451-1454
[6]   An improved catalyst for the cyclization/hydrosilylation of functionalized 1,6-dienes employing dimethylphenylsilane [J].
Widenhoefer, RA ;
Vadehra, A .
TETRAHEDRON LETTERS, 1999, 40 (49) :8499-8502
[7]   Cyclization/hydrosilylation of functionalized dienes catalyzed by a cationic palladium phenanthroline complex [J].
Widenhoefer, RA ;
Stengone, CN .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (23) :8681-8692
[8]   Tandem cyclization/hydrosilylation of functionalized 1,6-dienes catalyzed by a cationic palladium complex [J].
Widenhoefer, RA ;
DeCarli, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3805-3806