Cascade radical reaction of substrates with a carbon–carbon triple bond as a radical acceptor

Beilstein Journal of Organic Chemistry

Ryuta Asada¹  Yoshiji Takemoto¹  Hideto Miyabe² 

[1] Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan;School of Pharmacy, Hyogo University of Health Sciences, Minatojima, Chuo-ku, Kobe 650-8530, Japan;

关键词: cascade;    cyclization;    enantioselective;    free radical;    Lewis acid;    radical;   

DOI  :  10.3762/bjoc.9.128

来源: DOAJ

【 摘 要 】

The limitation of hydroxamate ester as a chiral Lewis acid coordination moiety was first shown in an intermolecular reaction involving a radical addition and sequential allylation processes. Next, the effect of hydroxamate ester was studied in the cascade addition–cyclization–trapping reaction of substrates with a carbon–carbon triple bond as a radical acceptor. When substrates with a methacryloyl moiety and a carbon–carbon triple bond as two polarity-different radical acceptors were employed, the cascade reaction proceeded effectively. A high level of enantioselectivity was also obtained by a proper combination of chiral Lewis acid and these substrates.

【 授权许可】

Unknown