Issue 3, 2013
From the journal:

Chemical Science

A visible-light-promoted aerobic C–H/C–N cleavage cascade to isoxazolidine skeletons†

Jin Xie,a   Qicai Xue,a   Hongming Jin,a   Huamin Li,a   Yixiang Chenga  and  Chengjian Zhu*ab  

* Corresponding authors

a State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. China
E-mail: cjzhu@nju.edu.cn

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, P. R. China

Abstract

The bicyclic isoxazolidine scaffolds are the ubiquitously recurring motifs in alkaloids. Despite of their facile biosynthesises in nature, the laboratory synthesis of these derivatives is still complicated. In this paper, the isoxazolidine derivatives are concisely constructed in one process with excellent stereoselectivity from simple tertiary amines through a C–H activation-retro-aza-Michael-oxidation-cyclization tandem sequence by means of visible-light. This protocol provides a concise approach to dactylicapnosinine derivatives.

Graphical abstract: A visible-light-promoted aerobic C–H/C–N cleavage cascade to isoxazolidine skeletons

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Article information

DOI
https://doi.org/10.1039/C2SC22131D
Article type
Edge Article
Submitted
03 Dec 2012
Accepted
03 Jan 2013
First published
04 Jan 2013

Chem. Sci., 2013,4, 1281-1286

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A visible-light-promoted aerobic C–H/C–N cleavage cascade to isoxazolidine skeletons

J. Xie, Q. Xue, H. Jin, H. Li, Y. Cheng and C. Zhu, Chem. Sci., 2013, 4, 1281 DOI: 10.1039/C2SC22131D

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