磺酰胺为烷基化试剂高选择性合成多取代烯烃和2,3-二氢茚衍生物的方法
收稿日期: 2015-04-15
修回日期: 2015-06-18
网络出版日期: 2015-08-25
High Regio- and Stereo-selective Synthesis of Polysubstituted Alkenes and Indane Derivatives Using N-Benzylic Sulfonamides as Alkylating Agents
Received date: 2015-04-15
Revised date: 2015-06-18
Online published: 2015-08-25
在质子酸H2SO4催化下, 含β氢醇与磺酰胺反应可高选择性地得到三取代烯烃和2,3-二氢茚衍生物. 含β氢醇酸性条件下脱水后与磺酰胺发生偶联, 可以选择性地合成热力学稳定产物Z-多取代烯烃; 两者发生[3+2]环加成反应, 则可高选择性地得到2,3-二氢茚衍生物.
关键词： 醇; 磺酰胺; 2,3-二氢茚衍生物; 立体选择性; [3+2]环加成
李海花 . 磺酰胺为烷基化试剂高选择性合成多取代烯烃和2,3-二氢茚衍生物的方法[J]. 有机化学, 2015 , 35(12) : 2568 -2574 . DOI: 10.6023/cjoc201504022
The reaction of alcohols with β-hydrogen and N-benzylic sulfonamide has been developed in the presence of H2SO4 for the synthesis of polysubstituted alkenes and indane derivatives with high stereoselectivity. Alcohol with β-hydrogen dehydrates and then couples with N-benzylic sulfonamide in the acidic conditions to selectively synthesize thermodynamic stability product Z-multisubstituted alkenes, which then lead to a [3+2] annulation reaction to selectively afford the indane derivatives.
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