Chemistry - A European Journal

, volume 24 , issue 1 , pages 62-66

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

Sheng-zheng Wang ¹

Guo Zhongjie ¹

Shuqiang Chen ²

Yan Jiang ²

Fan Zhang ¹

Xueying Liu ¹

Weiping Chen ¹

Chun-Quan Sheng ²

Hide authors affiliations Show authors affiliations: 2 affiliations

Department of Medicinal Chemistry, School of Pharmacy; Fourth Military Medical University; 169 Changle West Road Xi'an 710032 P. R. China |

Department of Medicinal Chemistry, School of Pharmacy; Second Military Medical University; 325 Guohe Road Shanghai 200433 P. R. China |

Publication type: Journal Article

Publication date: 2017-10-19

Wiley

Chemistry - A European Journal

scimago Q1

wos Q2

SJR: 0.981

CiteScore: 6.7

Impact factor: 3.7

ISSN: 09476539, 15213765

DOI: 10.1002/chem.201703837

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PubMed ID: 28940858

General Chemistry

Catalysis

Organic Chemistry

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).

Found

1 citation

Gavrilov Konstantin

DSc in Chemistry, professor

149 publications, 1 764 citations

h-index: 20

Ryazan State University named after S. A. Esenin

Research interests

Asymmetric metal complex catalysis

Asymmetric synthesis

Complex formation

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Wang S. et al. Organocatalytic Asymmetric Synthesis of Spiro-Tetrahydrothiophene Oxindoles Bearing Four Contiguous Stereocenters by One-Pot Michael-Henry-Cascade-Rearrangement Reactions // Chemistry - A European Journal. 2017. Vol. 24. No. 1. pp. 62-66.

GOST all authors (up to 50) Copy

Wang S., Zhongjie G., Chen S., Jiang Y., Zhang F., Liu X., Chen W., Sheng C. Organocatalytic Asymmetric Synthesis of Spiro-Tetrahydrothiophene Oxindoles Bearing Four Contiguous Stereocenters by One-Pot Michael-Henry-Cascade-Rearrangement Reactions // Chemistry - A European Journal. 2017. Vol. 24. No. 1. pp. 62-66.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1002/chem.201703837

UR - https://doi.org/10.1002/chem.201703837

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

T2 - Chemistry - A European Journal

AU - Wang, Sheng-zheng

AU - Zhongjie, Guo

AU - Chen, Shuqiang

AU - Jiang, Yan

AU - Zhang, Fan

AU - Liu, Xueying

AU - Chen, Weiping

AU - Sheng, Chun-Quan

PY - 2017

DA - 2017/10/19

PB - Wiley

SP - 62-66

IS - 1

VL - 24

PMID - 28940858

SN - 0947-6539

SN - 1521-3765

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2017_Wang,

author = {Sheng-zheng Wang and Guo Zhongjie and Shuqiang Chen and Yan Jiang and Fan Zhang and Xueying Liu and Weiping Chen and Chun-Quan Sheng},

title = {Organocatalytic Asymmetric Synthesis of Spiro-Tetrahydrothiophene Oxindoles Bearing Four Contiguous Stereocenters by One-Pot Michael-Henry-Cascade-Rearrangement Reactions},

journal = {Chemistry - A European Journal},

year = {2017},

volume = {24},

publisher = {Wiley},

month = {oct},

url = {https://doi.org/10.1002/chem.201703837},

number = {1},

pages = {62--66},

doi = {10.1002/chem.201703837}

}

MLA

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MLA Copy

Wang, Sheng-zheng, et al. “Organocatalytic Asymmetric Synthesis of Spiro-Tetrahydrothiophene Oxindoles Bearing Four Contiguous Stereocenters by One-Pot Michael-Henry-Cascade-Rearrangement Reactions.” Chemistry - A European Journal, vol. 24, no. 1, Oct. 2017, pp. 62-66. https://doi.org/10.1002/chem.201703837.

Publisher

Wiley

Journal

Chemistry - A European Journal

scimago Q1

wos Q2

SJR

0.981

CiteScore

6.7

Impact factor

3.7

ISSN

09476539 (Print)

15213765 (Electronic)