STEREOCHEMISTRY OF THE ADDITION OF ALPHA-METALATED N,N-DIMETHYLSULFONAMIDES TO 4-TERT-BUTYLCYCLOHEXANONE

被引：7
|
作者：
MLADENOVA, M [1 ]
GAUDEMARBARDONE, F [1 ]
机构：
[1] UNIV PARIS 06,SYNTHESE ORGANOMET LAB,F-75230 PARIS 05,FRANCE
来源：
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1990年 / 47卷 / 1-2期
关键词：
4-t-butylcyclohexanone; aldol reaction; axial (equatorial) attack; N; N-dimethyIsuIfonamides; N-dimethylamides of β-hydroxysulfonic acids; stereochemistry; α-Metallated;
D O I：
10.1080/10426509008046860
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The effects of some reaction conditions on the aldol reaction of RCH(M)S02N(CH,)2 and product stereochemistries are reported. Under thermodynamic control the reaction is nonstereoselective. Under kinetic control, stereoselectivity varies with R. For R = H, axial attack is slightly favoured, while equatorial attack is dominant for R = CH3 Dimethyl phenylmethanesulfonamide reacts highly stereoselectively. Equatorial attack is favoured with M = MgCI and M = Li, while M = Na gives 100% axial attack. These, and several more observations cannot be interpreted in terms of current concepts of nucleophilic additions to 4-t-butylcyclohexanone. © 1990, Taylor & Francis Group, LLC. All rights reserved.
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页码：191 / 197
页数：7
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