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Chemistry. 2018 Jan 2;24(1):62-66. doi: 10.1002/chem.201703837. Epub 2017 Oct 19.

Organocatalytic Asymmetric Synthesis of Spiro-Tetrahydrothiophene Oxindoles Bearing Four Contiguous Stereocenters by One-Pot Michael-Henry-Cascade-Rearrangement Reactions.

Author information

1
Department of Medicinal Chemistry, School of Pharmacy, Fourth Military Medical University, 169 Changle West Road, Xi'an, 710032, P. R. China.
2
Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai, 200433, P. R. China.

Abstract

Asymmetric construction of tetrahydrothiophenes with four contiguous stereocenters remains a formidable challenge. Herein, the bottleneck was addressed by an unprecedented one-pot Michael-Henry-cascade-rearrangement reaction that could simultaneously create four consecutive stereogenic centers including two tetrasubstituted carbon stereocenters. The highly functionalized chiral spirotetrahydrothiophene scaffolds were assembled in moderate to good yields (≈54-79 %), excellent diastereo- (>20:1 d.r.) and enantio-selectivities (up to 93 % ee).

KEYWORDS:

Michael-Henry reaction; asymmetric synthesis; organocatalysis; rearrangement; spiro-tetrahydrothiophene oxindoles

PMID:
28940858
DOI:
10.1002/chem.201703837

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