Asymmetric Net Cycloaddition for Access to Diverse Substituted 1,5-Benzothiazepines,The Journal of Organic Chemistry

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Asymmetric Net Cycloaddition for Access to Diverse Substituted 1,5-Benzothiazepines
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-11-14 00:00:00 , DOI: 10.1021/acs.joc.7b02451
Yukihiro Fukata ₁ , Koichi Yao ₁ , Ryota Miyaji ₁ , Keisuke Asano ₁ , Seijiro Matsubara ₁

Affiliation

In this study, the isothiourea-catalyzed enantioselective formal [4+3] cycloaddition of various α,β-unsaturated carboxylic acid derivatives with 2-aminothiophenols was developed. Mechanistic studies suggested that the reaction proceeds via a reversible sulfa-Michael addition to α,β-unsaturated acylammonium intermediates, followed by the enantioselective formation of a seven-membered ring, enabling the facile and divergent synthesis of optically active 2- and 3-substituted 1,5-benzothiazepines. This process was demonstrated to be highly versatile, affording the corresponding products in excellent regioselectivities and high enantioselectivities. Furthermore, this method enabled the synthesis of chiral 2,3-disubstituted 1,5-benzothiazepines in high regio-, enantio-, and diastereoselectivities. Hence, this protocol can be applied for the construction of a library of useful pharmaceutical candidates.

中文翻译：

非对称净环加成反应，可制得各种取代的1,5-苯并噻氮平

在这项研究中，开发了异硫脲催化的各种α，β-不饱和羧酸衍生物与2-氨基硫酚的对映体选择性[4 + 3]环加成反应。机理研究表明，反应是通过可逆的磺胺-迈克尔加成至α，β-不饱和酰基铵中间体而进行的，随后对映选择性地形成一个七元环，从而可以轻松，发散地合成旋光的2和3取代的旋光化合物。 1,5-苯并硫氮杂s类。事实证明，该方法具有高度的通用性，可提供具有出色的区域选择性和高对映选择性的相应产品。此外，该方法使得能够以高区域，对映体和非对映体选择性合成手性2，3-二取代的1，5-苯并硫氮杂s。因此，

更新日期：2017-11-16

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