A Convergent Approach to 1,3-Dithiolan-2-ones and an Unexpected Synthesis of Lactones

Xianzhu Zeng; Samir Z. Zard

doi:10.1021/acs.orglett.2c02215

A Convergent Approach to 1,3-Dithiolan-2-ones and an Unexpected Synthesis of Lactones

Xianzhu Zeng
, Samir Z. Zard

Laboratoire de Synthèse Organique

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

6 Citations (Scopus)

Abstract

A convergent route to 1,3-dithiolan-2-ones based on the radical addition of xanthates to allylic acetates is described. The process is modular, uses inexpensive starting materials and reagents, and is atom economical, since both sulfur atoms of the xanthate end up in the products. With adducts derived from xanthates bearing an ester group, an unexpected transformation leading to lactones was uncovered.

Original language	English
Pages (from-to)	5245-5248
Number of pages	4
Journal	Organic Letters
Volume	24
Issue number	29
DOIs	https://doi.org/10.1021/acs.orglett.2c02215
Publication status	Published - 29 Jul 2022
Externally published	Yes

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10.1021/acs.orglett.2c02215

Cite this

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title = "A Convergent Approach to 1,3-Dithiolan-2-ones and an Unexpected Synthesis of Lactones",

abstract = "A convergent route to 1,3-dithiolan-2-ones based on the radical addition of xanthates to allylic acetates is described. The process is modular, uses inexpensive starting materials and reagents, and is atom economical, since both sulfur atoms of the xanthate end up in the products. With adducts derived from xanthates bearing an ester group, an unexpected transformation leading to lactones was uncovered.",

author = "Xianzhu Zeng and Zard, \{Samir Z.\}",

year = "2022",

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doi = "10.1021/acs.orglett.2c02215",

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journal = "Organic Letters",

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AU - Zeng, Xianzhu

AU - Zard, Samir Z.

PY - 2022/7/29

Y1 - 2022/7/29

N2 - A convergent route to 1,3-dithiolan-2-ones based on the radical addition of xanthates to allylic acetates is described. The process is modular, uses inexpensive starting materials and reagents, and is atom economical, since both sulfur atoms of the xanthate end up in the products. With adducts derived from xanthates bearing an ester group, an unexpected transformation leading to lactones was uncovered.

AB - A convergent route to 1,3-dithiolan-2-ones based on the radical addition of xanthates to allylic acetates is described. The process is modular, uses inexpensive starting materials and reagents, and is atom economical, since both sulfur atoms of the xanthate end up in the products. With adducts derived from xanthates bearing an ester group, an unexpected transformation leading to lactones was uncovered.

U2 - 10.1021/acs.orglett.2c02215

DO - 10.1021/acs.orglett.2c02215

M3 - Article

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AN - SCOPUS:85135380091

SN - 1523-7060

VL - 24

SP - 5245

EP - 5248

JO - Organic Letters

JF - Organic Letters

IS - 29

ER -

A Convergent Approach to 1,3-Dithiolan-2-ones and an Unexpected Synthesis of Lactones

Abstract

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