One pot preparation of α-dithioacetal/α-diselenoacetal amides via a dual-C–S/C–Se bond formation and C–C bond cleavage cascade of 3-oxo-butanamides

Jiao-xia Zou; Yong-qiang Wang; Long-tao Huang; Yi Jiang; Jin-hong Chen; Long-qing Zhu; Yu-hang Yang; Yi-yue Feng; Xue Peng; Zhen Wang

doi:10.1039/C8QO00435H

One pot preparation of α-dithioacetal/α-diselenoacetal amides via a dual-C–S/C–Se bond formation and C–C bond cleavage cascade of 3-oxo-butanamides†‡

Jiao-xia Zou,§^a Yong-qiang Wang,§^a Long-tao Huang,^a Yi Jiang,

^a Jin-hong Chen,^a Long-qing Zhu,^a Yu-hang Yang,^a Yi-yue Feng,^a Xue Peng*^a and Zhen Wang

*^ab

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* Corresponding authors

^a School of Pharmacy, Lanzhou University, West Donggang Road. No. 199, Lanzhou 730000, China
E-mail: zhenw@lzu.edu.cn

^b State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China

Abstract

A new and practical approach to α-dithioacetal/α-diselenoacetal amides has been developed, combining sequential functionalization of amides and a C–C bond cleavage strategy. In this reaction, various α-dithioacetal/α-diselenoacetal amides from 3-oxo-butanamides were prepared in one step with good regioselectivity and functional group tolerance.

Organic Chemistry Frontiers

One pot preparation of α-dithioacetal/α-diselenoacetal amides via a dual-C–S/C–Se bond formation and C–C bond cleavage cascade of 3-oxo-butanamides†‡

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One pot preparation of α-dithioacetal/α-diselenoacetal amides via a dual-C–S/C–Se bond formation and C–C bond cleavage cascade of 3-oxo-butanamides

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