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

Journal of the American Chemical Society
Jian-Jun FengJunliang Zhang

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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Jan 15, 2016·Chemical Society Reviews·Quanjun WangHanmin Huang
May 21, 2016·Organic & Biomolecular Chemistry·James D Neuhaus, Michael C Willis
Apr 4, 2018·Organic & Biomolecular Chemistry·Yong-Sheng ZhengJi-Kai Liu
Jan 23, 2019·Chemical Communications : Chem Comm·Kai GaoHanfeng Ding
Jul 27, 2020·Chemistry : a European Journal·Barry M TrostJohnathan E Schultz
May 6, 2021·Organic & Biomolecular Chemistry·Tanumay SarkarTharmalingam Punniyamurthy
May 6, 2021·Chemical Communications : Chem Comm·Jiwen HeRenhua Fan

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