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Gharui C, Prakash S, Chopra D, et al. Organocatalytic asymmetric addition of thioglycolates to o-quinone methides: a route to 5-substituted-5H-benzoxathiepine-2(3H)-ones. Org Biomol Chem. 2020;18(15):2828-2833doi: 10.1039/d0ob00568a.
Gharui, C., Prakash, S., Chopra, D., & Pan, S. C. (2020). Organocatalytic asymmetric addition of thioglycolates to o-quinone methides: a route to 5-substituted-5H-benzoxathiepine-2(3H)-ones. Organic & biomolecular chemistry, 18(15), 2828-2833. https://doi.org/10.1039/d0ob00568a
Gharui, Chandan, et al. "Organocatalytic asymmetric addition of thioglycolates to o-quinone methides: a route to 5-substituted-5H-benzoxathiepine-2(3H)-ones." Organic & biomolecular chemistry vol. 18,15 (2020): 2828-2833. doi: https://doi.org/10.1039/d0ob00568a
Gharui C, Prakash S, Chopra D, Pan SC. Organocatalytic asymmetric addition of thioglycolates to o-quinone methides: a route to 5-substituted-5H-benzoxathiepine-2(3H)-ones. Org Biomol Chem. 2020 Apr 15;18(15):2828-2833. doi: 10.1039/d0ob00568a. PMID: 32236238.
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Org Biomol Chem. 2020 Apr 15;18(15):2828-2833. doi: 10.1039/d0ob00568a.

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

Organic & biomolecular chemistry

Chandan Gharui, Satya Prakash, Deepak Chopra, Subhas Chandra Pan

Affiliations

  1. Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati, Assam 781039, India. [email protected].
  2. Department of Chemistry, Indian Institute of Science Education and Research, Bhopal, India. [email protected].

PMID: 32236238 DOI: 10.1039/d0ob00568a

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.

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