Catalyst-Controlled Switch in Diastereoselectivities: Enantioselective Construction of Functionalized 3,4-Dihydro-2H-thiopyrano[2,3-b]quinolines with Three Contiguous Stereocenters

Xin-Ni Ping,Pei-Shun Wei,Xiao-Qian Zhu,Jian-Wu Xie

JOURNAL OF ORGANIC CHEMISTRY（2017）

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Abstract

A tandem Michael-Henry reaction of 2-mercaptoquinoline-3-carbaldehydes with nitroolefins using hydrogen-bonding-based cooperative organocatalysts for the highly diastereodivergent synthesis of chiral functionalized 3,4-dihydro-2H-thiopyrano[2,3-b]quinolines with three contiguous tertiary stereocenters has been developed.

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Key words

enantioselective construction,34-dihydro-2<i>h</i>-thiopyrano23-<i>b</i>quinolines,diastereoselectivities,catalyst-controlled

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Catalyst-Controlled Switch in Diastereoselectivities: Enantioselective Construction of Functionalized 3,4-Dihydro-2H-thiopyrano­[2,3-b]­quinolines with Three Contiguous Stereocenters

Catalyst-Controlled Switch in Diastereoselectivities: Enantioselective Construction of Functionalized 3,4-Dihydro-2H-thiopyrano[2,3-b]quinolines with Three Contiguous Stereocenters