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Issue 15, 2020
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Organocatalytic asymmetric addition of thioglycolates to o-quinone methides: a route to 5-substituted-5H-benzoxathiepine-2(3H)-ones†

Chandan Gharui,a   Satya Prakash,b   Deepak Chopra ORCID logo b  and  Subhas Chandra Pan ORCID logo *a  
Author affiliations

* Corresponding authors

a Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati, Assam, India
E-mail: span@iitg.ac.in
Fax: +91-361-258-2349
Tel: +91-361-258-3304

b Department of Chemistry, Indian Institute of Science Education and Research, Bhopal, India
E-mail: dchopra@iiserb.ac.in

Abstract

Herein we have developed the first enantioselective synthesis of 5-substituted-5H-benzoxathiepine-2(3H)-ones. 2-Sulfonylmethyl phenols and thioglycolates were employed as reaction partners in this method. The desired thia Michael products were obtained via bifunctional squaramide catalyzed conjugate addition reaction to in situ generated o-quinone methides and then basic hydrolysis followed by cyclization led to the formation of 5-substituted-5H-benzoxathiepine-2(3H)-ones. Broad scope and moderate to high enantioselectivities were observed for both products.

Graphical abstract: Organocatalytic asymmetric addition of thioglycolates to o-quinone methides: a route to 5-substituted-5H-benzoxathiepine-2(3H)-ones

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Article information

https://doi.org/10.1039/D0OB00568A
Submitted
17 Mar 2020
Accepted
25 Mar 2020
First published
25 Mar 2020
Org. Biomol. Chem., 2020,18, 2828-2833
Article type
Communication
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Organocatalytic asymmetric addition of thioglycolates to o-quinone methides: a route to 5-substituted-5H-benzoxathiepine-2(3H)-ones

C. Gharui, S. Prakash, D. Chopra and S. C. Pan, Org. Biomol. Chem., 2020, 18, 2828
DOI: 10.1039/D0OB00568A

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