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. 2015 Mar 25;137(11):3787-90.
doi: 10.1021/jacs.5b01305. Epub 2015 Mar 16.

Transfer of chirality in the rhodium-catalyzed intramolecular formal hetero-[5 + 2] cycloaddition of vinyl aziridines and alkynes: stereoselective synthesis of fused azepine derivatives

Jian-Jun Feng  1 , Tao-Yan Lin  1 , Hai-Hong Wu  1 , Junliang Zhang  1
Affiliations

Transfer of chirality in the rhodium-catalyzed intramolecular formal hetero-[5 + 2] cycloaddition of vinyl aziridines and alkynes: stereoselective synthesis of fused azepine derivatives

Jian-Jun Feng et al. J Am Chem Soc. .

Abstract

By taking advantage of vinyl aziridines as a heteroatom-containing five-atom component in rhodium-catalyzed intramolecular formal hetero-[5 + 2] cycloaddition reactions with alkynes, a highly efficient method for the synthesis of fused azepine derivatives at 30 °C was developed. The reaction has broad substrate scope and tolerates a wide range of functional groups. The chirality of vinyl aziridine-alkyne substrates can be completely transferred to the cycloadducts, representing an atom-economic and enantiospecific protocol for the construction of fused 2,5-dihydroazepines for the first time.

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