期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 137, 期 16, 页码 5320-5323出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b02537
关键词
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资金
- Japanese Ministry of Education, Culture, Sports, Science and Technology
- Asahi Glass Foundation
- Toyota Physical and Chemical Research Institute
- Tokyo Institute of Technology Foundation
- Grants-in-Aid for Scientific Research [15J06653, 25888012] Funding Source: KAKEN
The 1,5-benzothiazepine moiety is well-known as a versatile pharmacophore, and its derivatives are expected to have antagonism against numerous diseases. Thus, it is desirable to develop a synthetic route that enables facile enantioselective preparation of a wide range of such derivatives. Although the cycloaddition approach could be considered a possible route to these compounds, to date, there has been no precedent of such a protocol. We therefore present the first example of a highly enantioselective net [4 + 3] cycloaddition to afford 1,5-benzothiazepines by utilizing alpha,beta-unsaturated acylammonium intermediates generated by chiral isothiourea catalysts, which undergo two sequential chemoselective nucleophilic attacks by 2-aminothiophenols. This protocol provided cycloadducts in extremely high regioselectivity, with a good-to-excellent stereoselectivity being achieved regardless of the steric and electronic properties of the substrates. This method therefore offers promising synthetic routes for the construction of a library of optically active 1,5-benzothiazepines for assay evaluation.
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