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Catalytic Asymmetric Iodoesterification of Simple Alkenes

2020; Wiley; Volume: 59; Issue: 31 Linguagem: Inglês

10.1002/anie.202003886

1521-3773

Takayoshi Arai, Kodai Horigane, Takumi Suzuki, Ryosuke Itoh, Masahiro Yamanaka,

Chemical Synthesis and Reactions

Catalytic asymmetric iodoesterification of simple alkenes was achieved using a dinuclear zinc-3,3'-(R,S,S)-bis(aminoimino)binaphthoxide (di-Zn) complex. For iodoesterification using p-methoxybenzoic acid, the N-iodonaphthalenimide (NIN)-I2 system was effective for producing iodoesters in a highly enantioselective manner. The synthetic utility of chiral iodo-p-methoxybenzoates was also demonstrated. The quartet of metal ionic bond, hydrogen bond, halogen bond, and π-π stacking is harmonized on the single reaction sphere of di-Zn catalyst for enabling the highly enantioselective catalytic asymmetric iodoesterification of simple alkenes for the first time.