Stereocontrol in an intermolecular Schmidt reaction of equilibrating hydroxyalkyl allylic azides

Ruzhang Liu; Juan Wang; Hao Wu; Xianfeng Quan; Shilin Wang; Jiandong Guo; Yang Wang; Heting Li

doi:10.1039/D4CC00907J

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Stereocontrol in an intermolecular Schmidt reaction of equilibrating hydroxyalkyl allylic azides†

Ruzhang Liu,

*^a Juan Wang,^a Hao Wu,^a Xianfeng Quan,^a Shilin Wang,^a Jiandong Guo,^a Yang Wang

^a and Heting Li^a

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* Corresponding authors

^a School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China
E-mail: liurzh@yzu.edu.cn

Abstract

A selective intermolecular Schmidt reaction of equilibrating hydroxyalkyl allylic azides is reported to afford N-hydroxyalk-1-en-3-yl lactams in modest to high yields. For prochiral and chiral ketones, modest to high 1,5-diastereoselectivity was achieved, and the mechanistic analysis is supported by DFT calculation.

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DOI: https://doi.org/10.1039/D4CC00907J
Article type: Communication
Submitted: 27 Feb 2024
Accepted: 25 Mar 2024
First published: 26 Mar 2024

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Chem. Commun., 2024,60, 4362-4365

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Stereocontrol in an intermolecular Schmidt reaction of equilibrating hydroxyalkyl allylic azides

R. Liu, J. Wang, H. Wu, X. Quan, S. Wang, J. Guo, Y. Wang and H. Li, Chem. Commun., 2024, 60, 4362 DOI: 10.1039/D4CC00907J

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Chemical Communications

Stereocontrol in an intermolecular Schmidt reaction of equilibrating hydroxyalkyl allylic azides†

Abstract

Supplementary files

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Stereocontrol in an intermolecular Schmidt reaction of equilibrating hydroxyalkyl allylic azides

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