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Short Paper | Special issue | Vol 103, No. 2, 2021, pp.1078-1098
Published online, 17th February, 2021
DOI: 10.3987/COM-20-S(K)61
Diastereo- and Enantioselective Intramolecular 1,6-C–H Insertion Reaction of Diaryldiazomethanes Catalyzed by Chiral Dirhodium(II) Carboxylates

Motoki Ito, Yuji Kondo, Ryosuke Namie, Yoshihiro Natori, Koji Takeda, Hisanori Nambu, Masahiro Anada,* Yasunori Yamamoto, and Shunichi Hashimoto*

*Faculty of Pharmacy, Musasino University, Shinmachi 1-1-20, Nishitokyo, Tokyo, Japan

Abstract

A highly diastereo- and enantioselective intramolecular 1,6-C–H insertion reaction of diaryldiazomethanes possessing an ether group has been achieved with the use of dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] as a catalyst, providing exclusively 3-substituted cis-3,4-dihydro-4-phenyl-1H-isochromans in up to 99% ee with no evidence of tandem ylide formation–rearrangement.