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One-pot synthesis of chiral β-hydroxysulfones from alkynes via aerobic oxysulfonylation and asymmetric reduction in MeOH/H2O

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Abstract

A highly enantioselective synthesis of β-hydroxysulfones from inexpensive and readily available terminal alkynes and sodium sulfinates via a consecutive one-pot reaction in an aqueous medium under mild conditions is described. The intermediates, β-keto sulfones, generated from an aerobic oxysulfonylation of terminal alkynes and sodium sulfinates catalyzed by an iron salt in MeOH/H2O (v : v = 3 : 1) at 50 °C, were subsequently reduced by a Ru-catalyzed asymmetric transfer hydrogenation with HCOONa as a hydrogen source. A variety of chiral β-hydroxysulfones were obtained in good yields and up to 99.9% ee values. This one-pot process could be easily scaled up for gram-scale synthesis.

Graphical abstract: One-pot synthesis of chiral β-hydroxysulfones from alkynes via aerobic oxysulfonylation and asymmetric reduction in MeOH/H2O

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Publication details

The article was received on 23 Nov 2018, accepted on 10 Jan 2019 and first published on 11 Jan 2019


Article type: Paper
DOI: 10.1039/C8GC03671C
Citation: Green Chem., 2019, Advance Article
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    One-pot synthesis of chiral β-hydroxysulfones from alkynes via aerobic oxysulfonylation and asymmetric reduction in MeOH/H2O

    P. Cui, Q. Liu, J. Wang, H. Liu and H. Zhou, Green Chem., 2019, Advance Article , DOI: 10.1039/C8GC03671C

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