使用有机催化对映选择性串联迈克尔-亨利反应合成2,3,4-三取代硫代色满
Synthesis of 2,3,4-Trisubstituted Thiochromanes using an Organocatalytic Enantioselective Tandem Michael-Henry Reaction.
作者信息
Dodda Rajasekhar, Goldman Joshua J, Mandal Tanmay, Zhao Cong-Gui, Broker Grant A, Tiekink Edward R T
机构信息
Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, ; e-mail:
出版信息
Adv Synth Catal. 2008 Feb 26;350(4):537-541. doi: 10.1002/adsc.200700331.
Abstract
Enantioenriched 2,3,4-trisubstituted thiochromanes have been synthesized by using a cupreine-catalyzed tandem Michael addition-Henry reaction between 2-mercaptobenzaldehydes and β-nitrostyrenes. Good diastereoselectivities and enantioselectivities were obtained for the title compounds, which may be further improved through a single recrystallization (up to 98% de and> 99% ee).
摘要
通过使用铜试剂催化的2-巯基苯甲醛与β-硝基苯乙烯之间的串联迈克尔加成-亨利反应，合成了对映体富集的2,3,4-三取代硫代色满。对于标题化合物获得了良好的非对映选择性和对映选择性，通过单次重结晶可进一步提高（高达98%的非对映体过量和>99%的对映体过量）。
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