Synthesis of 2-Aryl-3-sulfonylchromans via Knoevenagel Condensation and Reduction Protocol

Meng-Yang Chang; Han-Yu Chen; Yu-Hsin Chen

doi:10.1021/acs.joc.7b02392

Synthesis of 2-Aryl-3-sulfonylchromans via Knoevenagel Condensation and Reduction Protocol

J Org Chem. 2017 Dec 1;82(23):12631-12639. doi: 10.1021/acs.joc.7b02392. Epub 2017 Nov 9.

Authors

Meng-Yang Chang¹, Han-Yu Chen¹, Yu-Hsin Chen¹

Affiliation

¹ Department of Medicinal and Applied Chemistry, Kaohsiung Medical University Hospital, Kaohsiung Medical University , Kaohsiung 807, Taiwan.

PMID: 29094936
DOI: 10.1021/acs.joc.7b02392

Abstract

In this article, a concise, easy-operational, and high-yield method for the synthesis of 2-aryl-3-sulfonylchromans is described by two-step routes: (i) NH₄OAc mediated Knoevenagel condensation of β-ketosulfones and o-hydroxybenzaldehydes in a cosolvent of toluene and THF at reflux for 10 h, and (ii) NaBH₄ promoted regio- and stereocontrolled reduction of the resulting 2-arylchromen-2-ols in a cosolvent of MeOH and THF at rt for 1 h. This protocol provides a highly effective (4+2) annulation via one carbon-oxygen and one carbon-carbon bond formations.

Publication types

Research Support, Non-U.S. Gov't