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

ABSTRACT: 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.

SUBMITTER: Miyabe H

PROVIDER: S-EPMC3701377 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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

Miyabe Hideto H Asada Ryuta R Takemoto Yoshiji Y

Beilstein journal of organic chemistry 20130613

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, t ...[more]

PMID: 23843907

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