Intramolecular Imino-ene Reaction of Azirines: Regioselectivity, Diastereoselectivity, and Computational Insights

The Journal of Organic Chemistry
Mei-Hua ShenHua-Dong Xu

Abstract

Intramolecular imino-ene reaction of 2 H-aziridine has been studied experimentally and computationally, demonstrating that (1) the concerted process takes place regioselectively on the alkene E-CH group; (2) the geometry of the N-linker impacts the reaction activation energy and diastereoselectivity significantly, with pyramidal alkyl amine as the linkage, an exclusive cis-product is achieved; (3) when the reaction has to occur with the Z-CH group, the cis-diastereoselectivity is solely observed regardless of the nature of the N-linkage.

References

Apr 12, 2003·The Journal of Organic Chemistry·Masamichi YamanakaMasako Nakagawa
Feb 1, 1965·The Journal of Organic Chemistry·D F MORROWE C HUANG
Apr 20, 2006·Chemical Communications : Chem Comm·Daniel MortonRobert A Stockman
Nov 8, 2008·Physical Chemistry Chemical Physics : PCCP·Jeng-Da Chai, Martin Head-Gordon
Nov 18, 2010·Angewandte Chemie·Bo HanYing-Chun Chen
Jul 28, 2011·Organic & Biomolecular Chemistry·Qiwu YangWenqin Zhang

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