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Highly enantioselective addition of phenylethynylzinc to aldehydes catalyzed by chiral cyclopropane-based amino alcohols.

ABSTRACT: The enantioselective addition of phenylethynylzinc to aldehydes catalyzed by a series of cyclopropane-based amino alcohol ligands 7 was investigated. The reactions afforded chiral propargylic alcohols in high yields (up to 96%) and with excellent enantioselectivities (up to 98% ee) under mild conditions. Furthermore, studies on the structural relationship show that the matching of the chiral center configuration is crucial to obtain the high enantioselectivity.

SUBMITTER: Zheng B

PROVIDER: S-EPMC6270052 | biostudies-literature | 2013 Dec

REPOSITORIES: biostudies-literature

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Highly enantioselective addition of phenylethynylzinc to aldehydes catalyzed by chiral cyclopropane-based amino alcohols.

Zheng Bing B Li Zhiyuan Z Liu Feipeng F Wu Yanhua Y Shen Junjian J Bian Qinghua Q Hou Shicong S Wang Ming M

Molecules (Basel, Switzerland) 20131211 12

The enantioselective addition of phenylethynylzinc to aldehydes catalyzed by a series of cyclopropane-based amino alcohol ligands 7 was investigated. The reactions afforded chiral propargylic alcohols in high yields (up to 96%) and with excellent enantioselectivities (up to 98% ee) under mild conditions. Furthermore, studies on the structural relationship show that the matching of the chiral center configuration is crucial to obtain the high enantioselectivity. ...[more]

PMID: 24335619

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