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Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond Cleavage.

ABSTRACT: An iron-catalyzed highly anti-Markovnikov selective, enantioselective hydrosilylation of vinylcyclopropanes with PhSiH₃ was reported for the preparation of valuable chiral allylic silanes via stereospecific C-C bond cleavage. Simultaneously, difficultly prepared chiral VCPs could be also obtained with moderate to excellent enantioselectivity via this kinetic resolution pathway. The chiral Z-allylic silanes could be converted to various chiral allylic derivatives. A possible mechanism via an iron-silyl species was proposed based on experimental and computational studies.

SUBMITTER: Chen C

PROVIDER: S-EPMC7115165 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond Cleavage.

Chen Chenhui C Wang Hongliang H Sun Yufeng Y Cui Jiayan J Xie Jianbo J Shi Yang Y Yu Shijia S Hong Xin X Lu Zhan Z

iScience 20200317 4

An iron-catalyzed highly anti-Markovnikov selective, enantioselective hydrosilylation of vinylcyclopropanes with PhSiH<sub>3</sub> was reported for the preparation of valuable chiral allylic silanes via stereospecific C-C bond cleavage. Simultaneously, difficultly prepared chiral VCPs could be also obtained with moderate to excellent enantioselectivity via this kinetic resolution pathway. The chiral Z-allylic silanes could be converted to various chiral allylic derivatives. A possible mechanism ...[more]

PMID: 32240952

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