ChemInform Abstract: Approaches to 2,6‐Diaryl‐3,7‐dioxabicyclo(3.3.0)octane Lignans via Asymmetric Synthesis of Dihydro‐ and Tetrahydrofuran Derivatives.

Abstract

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Synthesis and Reactions of 2-Chlorovinyl Sulfones

“…Thus, treatment of 2,2-dichloroethanesulfonylarenes with Et 3 N [18,19], Et 3 N / PhH [20][21][22] or Et 3 N / CH 2 Cl 2 [23] selectively leads to formation only of E-isomers of 2-chlorovinyl sulfones. For example, reaction of 2,2-dichloroethanesulfonylbenzene (10) with Et 3 N in mixture of diethyl ether and dichloromethane at 15 o C afforded product (E)-5 in 97% yield [24]. Treatment of benzene sulfonyl chloride (11) with naphthalene-1,4-diyldiamine hydrochloride in the presence of AlCl 3 in chloroform and then with Et 3 N afforded (E)-5 in 78% yield [21].…”

“…Synthesis of 2,3-dihydrofuran derivatives from 2-chlorovinyl sulfones was described in some articles [18,24,30,43,44]. Thus, interaction of epoxy alcohol 47 with chlorovinyl sulfone 5 afforded intermediate ether 48.…”