Enantioselective Synthesis of N−H-Free 1,5-Benzothiazepines

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• 作者：Guojin Wang ; Yu Tang ; Yu Zhang ; Prof. Dr. Xiaohua Liu ; Dr. Lili Lin and Prof. Dr. Xiaoming Feng
• 刊名：Chemistry - A European Journal
• 出版年：2017
• 出版时间：January 12, 2017
• 年：2017
• 卷：23
• 期：3
• 页码：554-557
• 全文大小：509K
• ISSN：1521-3765

文摘

An enantioselective sulfa-Michael-cyclization reaction was developed for the synthesis of 1,5-benzothiazepines with versatile pharmacological activities. The reaction between 2-aminothiophenol and α,β-unsaturated pyrazoleamides gave direct access to N−H-free 1,5-benzothiazepines in the presence of a chiral N,N′-dioxide/Yb(OTf)₃ complex. Excellent enantioselectivities (up to 96 % ee) and high yields (up to 99 %) were obtained for a broad range of substrates under mild reaction conditions. This method provided a facile approach to the antidepressant drug (R)-(−)-Thiazesim.