Asymmetric synthesis of chiral dihydrothiopyrans via an organocatalytic enantioselective formal thio [3 + 3] cycloaddition reaction with binucleophilic bisketone thioethers

Shengzheng Wang; Yongqiang Zhang; Guoqiang Dong; Shanchao Wu; Shiping Zhu; Zhenyuan Miao; Jianzhong Yao; Hao Li; Jian Li; Wannian Zhang; Chunquan Sheng; Wei Wang

doi:10.1021/ol4027705

Asymmetric synthesis of chiral dihydrothiopyrans via an organocatalytic enantioselective formal thio [3 + 3] cycloaddition reaction with binucleophilic bisketone thioethers

Shengzheng Wang, Yongqiang Zhang, Guoqiang Dong, Shanchao Wu, Shiping Zhu, Zhenyuan Miao, Jianzhong Yao, Hao Li, Jian Li, Wannian Zhang, Chunquan Sheng, Wei Wang

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

An unprecedented organocatalytic highly enantioselective approach to a 3,4-dihydro-2H-thiopyran scaffold with two contiguous stereogenic centers has been implemented through a formal thio [3 + 3] cycloaddition process involving a Michael-aldol condensation cascade sequence. Notably, a new class of binucleophilic bisketone thioethers is designed for the process. Furthermore, the fine-tuning of their reactivity enables the cascade process to proceed with highly regioselectively.

Original language	English (US)
Pages (from-to)	5570-5573
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	21
DOIs	https://doi.org/10.1021/ol4027705
State	Published - Nov 1 2013
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol4027705

Cite this

@article{ec7b2b4279854d41988be0323fbc888c,

title = "Asymmetric synthesis of chiral dihydrothiopyrans via an organocatalytic enantioselective formal thio [3 + 3] cycloaddition reaction with binucleophilic bisketone thioethers",

abstract = "An unprecedented organocatalytic highly enantioselective approach to a 3,4-dihydro-2H-thiopyran scaffold with two contiguous stereogenic centers has been implemented through a formal thio [3 + 3] cycloaddition process involving a Michael-aldol condensation cascade sequence. Notably, a new class of binucleophilic bisketone thioethers is designed for the process. Furthermore, the fine-tuning of their reactivity enables the cascade process to proceed with highly regioselectively.",

author = "Shengzheng Wang and Yongqiang Zhang and Guoqiang Dong and Shanchao Wu and Shiping Zhu and Zhenyuan Miao and Jianzhong Yao and Hao Li and Jian Li and Wannian Zhang and Chunquan Sheng and Wei Wang",

year = "2013",

month = nov,

day = "1",

doi = "10.1021/ol4027705",

language = "English (US)",

volume = "15",

pages = "5570--5573",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Asymmetric synthesis of chiral dihydrothiopyrans via an organocatalytic enantioselective formal thio [3 + 3] cycloaddition reaction with binucleophilic bisketone thioethers

AU - Wang, Shengzheng

AU - Zhang, Yongqiang

AU - Dong, Guoqiang

AU - Wu, Shanchao

AU - Zhu, Shiping

AU - Miao, Zhenyuan

AU - Yao, Jianzhong

AU - Li, Hao

AU - Li, Jian

AU - Zhang, Wannian

AU - Sheng, Chunquan

AU - Wang, Wei

PY - 2013/11/1

Y1 - 2013/11/1

N2 - An unprecedented organocatalytic highly enantioselective approach to a 3,4-dihydro-2H-thiopyran scaffold with two contiguous stereogenic centers has been implemented through a formal thio [3 + 3] cycloaddition process involving a Michael-aldol condensation cascade sequence. Notably, a new class of binucleophilic bisketone thioethers is designed for the process. Furthermore, the fine-tuning of their reactivity enables the cascade process to proceed with highly regioselectively.

AB - An unprecedented organocatalytic highly enantioselective approach to a 3,4-dihydro-2H-thiopyran scaffold with two contiguous stereogenic centers has been implemented through a formal thio [3 + 3] cycloaddition process involving a Michael-aldol condensation cascade sequence. Notably, a new class of binucleophilic bisketone thioethers is designed for the process. Furthermore, the fine-tuning of their reactivity enables the cascade process to proceed with highly regioselectively.

UR - http://www.scopus.com/inward/record.url?scp=84887102700&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84887102700&partnerID=8YFLogxK

U2 - 10.1021/ol4027705

DO - 10.1021/ol4027705

M3 - Article

C2 - 24152030

AN - SCOPUS:84887102700

SN - 1523-7060

VL - 15

SP - 5570

EP - 5573

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Asymmetric synthesis of chiral dihydrothiopyrans via an organocatalytic enantioselective formal thio [3 + 3] cycloaddition reaction with binucleophilic bisketone thioethers

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this