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Organocatalytic Asymmetric Addition of Thioglycolates to o-Quinone Methides: A Route to 5-substituted-5H-benzoxathiepine-2(3H)-ones

Abstract

Here in we have developed the first enantioselective synthesis of 5-substituted-5H-benzoxathiepine-2(3H)-ones. 2-Sulfonylmethyl phenols and thioglycolates were employed as the 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.

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Article information


Submitted
17 Mar 2020
Accepted
25 Mar 2020
First published
25 Mar 2020

Org. Biomol. Chem., 2020, Accepted Manuscript
Article type
Communication

Organocatalytic Asymmetric Addition of Thioglycolates to o-Quinone Methides: A Route to 5-substituted-5H-benzoxathiepine-2(3H)-ones

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

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