Silylation-Based Kinetic Resolution of Monofunctional Secondary Alcohols

被引:68
作者
Sheppard, Cody I. [1 ]
Taylor, Jessica L. [1 ]
Wiskur, Sheryl L. [1 ]
机构
[1] Univ S Carolina, Dept Chem & Biochem, Columbia, SC 29208 USA
基金
美国国家科学基金会;
关键词
ENANTIOSELECTIVE ACYLATION; STEREOSELECTIVE SILYLATION; CATALYST; HYDROGENATION; ROTATION; CRYSTAL; SILANES;
D O I
10.1021/ol2012617
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The nucleophilic small molecule catalyst (-)-tetramisole was found to catalyze the kinetic resolution of monofunctional secondary alcohols via enantioselective silylation. Optimization of this new methodology allows for selectivity factors up to 25 utilizing commercially available reagents and mild reaction conditions.
引用
收藏
页码:3794 / 3797
页数:4
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[1]   CONFORMATIONAL-ANALYSIS OF GROUP IVB ARYLS - AN ELECTRIC BIREFRINGENCE AND MOLECULAR MECHANICS STUDY [J].
ALLEN, GW ;
ARONEY, MJ ;
HAMBLEY, TW .
JOURNAL OF MOLECULAR STRUCTURE, 1990, 216 :227-240
[2]  
Andersson P. G., 2008, Modern Reduction Methods
[3]  
[Anonymous], 1999, PROTECTIVE GROUPS OR
[4]   MOLECULAR POLARISABILITY . CONFORMATIONS OF TRIPHENYLSILANE CHLOROTRIPHENYLSILANE AND BROMOTRIPHENYLSILANE AS SOLUTES IN BENZENE [J].
ARONEY, MJ ;
LEFEVRE, RJW ;
RITCHIE, GLD ;
ROSS, V .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1966, (02) :188-&
[5]   CRYSTAL AND MOLECULAR-STRUCTURE OF TRIPHENYLSILYLTHIIRANE [J].
BARBIERI, G ;
ANDREETTI, GD ;
BOCELLI, G ;
SGARABOTTO, P .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 172 (03) :285-291
[6]   Benzotetramisole: A remarkably enantioselective acyl transfer catalyst [J].
Birman, VB ;
Li, XM .
ORGANIC LETTERS, 2006, 8 (07) :1351-1354
[7]   Homobenzotetramisole: An effective catalyst for kinetic resolution of aryl-cycloalkanols [J].
Birman, Vladimir B. ;
Li, Ximin .
ORGANIC LETTERS, 2008, 10 (06) :1115-1118
[8]   Kinetic resolution of propargylic alcohols catalyzed by benzotetramisole [J].
Birman, Vladimir B. ;
Guo, Lei .
ORGANIC LETTERS, 2006, 8 (21) :4859-4861
[9]   Combined lipase-catalyzed resolution/Mitsunobu esterification for the production of enantiomerically enriched arylalkyl carbinols [J].
Bouzemi, N ;
Aribi-Zouioueche, L ;
Fiaud, JC .
TETRAHEDRON-ASYMMETRY, 2006, 17 (05) :797-800
[10]   On the use of succinic anhydride as acylating agent for practical resolution of aryl-alkyl alcohols through lipase-catalyzed acylation [J].
Bouzemi, N ;
Debbeche, H ;
Aribi-Zouioueche, L ;
Fiaud, JC .
TETRAHEDRON LETTERS, 2004, 45 (03) :627-630