Title

Cycloaddition/Ring Opening Reaction Sequences of N -Alkenyl Aziridines: Influence of the Aziridine Nitrogen on Stereoselectivity

Abstract

The cycloaddition of (Z)-7-(prop-1-enyl)-7-azabicyclo[4.1.0]heptane with dimethyl acetylene dicarboxylate (DMAD) was reported previously to proceed with complete stereoselectivity. Quantum chemical calculations (B3LYP) were used to evaluate the mechanism of the cyclization process, and it was discovered that a stepwise pathway is preferred. The subsequent electrocyclic ring opening reaction of the cyclobutene was also studied, and it was found that ring opening to the "methyl-in" dienamine is preferred to the "methyl-out" product by some 4-5 kcal/mol.

Department(s)

Chemistry

Document Type

Article

DOI

https://doi.org/10.1021/ol702623d

Keywords

aziridines, cyclization, stereoselectivity, chemical structure, nitrogen

Publication Date

2008

Recommended Citation

Siebert, Matthew R., Andrei K. Yudin, and Dean J. Tantillo. "Cycloaddition/Ring opening reaction sequences of n-alkenyl aziridines: influence of the aziridine nitrogen on stereoselectivity." Organic letters 10, no. 1 (2008): 57-60.

Journal Title

Organic letters

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