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

35 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

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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",

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doi = "10.1021/ol4027705",

language = "English (US)",

volume = "15",

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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.

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ER -

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

Abstract

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