Intermolecular Catalytic Asymmetric Iodoetherification of Unfunctionalized Alkenes

Takumi K Suzuki; Masahiro Yamanaka; Takayoshi Arai

doi:10.1021/acs.orglett.2c01490

Intermolecular Catalytic Asymmetric Iodoetherification of Unfunctionalized Alkenes

Org Lett. 2022 Jun 3;24(21):3872-3877. doi: 10.1021/acs.orglett.2c01490. Epub 2022 May 23.

Authors

Takumi K Suzuki¹, Masahiro Yamanaka², Takayoshi Arai¹

Affiliations

¹ Soft Molecular Activation Research Center (SMARC), Chiba Iodine Resource Innovation Center (CIRIC), Molecular Chirality Research Center (MCRC), Synthetic Organic Chemistry, Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan.
² Department of Chemistry, Rikkyo University, 3-34-1 Nishi-Ikebukuro, Toshima-ku, Tokyo 171-8501, Japan.

PMID: 35604948
DOI: 10.1021/acs.orglett.2c01490

Abstract

A newly prepared trinuclear Zn₃-(R,S,S)-aminoiminobinaphthoxide complex (triZn-II) catalyzed the first general intermolecular asymmetric iodoetherification of unfunctionalized alkenes. Using triZn-II, the iodoetherification reaction of unfunctionalized alkenes with o-nitrophenols proceeded smoothly to give the products with up to 92.5:7.5 er, and diene substrates were converted to the products with up to 99:1 er with the formation of a meso-isomer (dl/meso = 78/22). The chiral iodoethers gave a new platform for the synthesis of chiral morpholines.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes* / chemistry
Catalysis
Stereoisomerism

Substances

Alkenes