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Issue 47, 2018
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Copper-catalyzed diastereoselective synthesis of β-boryl-α-quaternary carbon carboxylic esters

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Abstract

Cu(I)-Catalyzed diastereoselective carboboration of α-alkyl-substituted α,β-unsaturated carboxylic esters to produce β-boryl-α-quaternary carbon esters was developed. The carbon skeletons of dialkyl sulfates, primary allyl halides, and benzyl bromides were transferred to the α-position of the substrates to provide products in moderate to good yields with a diastereoselectivity of >95% in most cases. Substrates bearing a β-(hetero)aryl substituent gave higher diastereoselectivities than those bearing a linear β-alkyl substituent. The crystal structure of the potassium trifluoroborate derivative shows that the reactions probably go through a copper(I) enolate intermediate and the diastereoselectivity arises from the electrophilic attack of electrophiles to the less hindered side of the enolates.

Graphical abstract: Copper-catalyzed diastereoselective synthesis of β-boryl-α-quaternary carbon carboxylic esters

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Publication details

The article was received on 04 Oct 2018, accepted on 19 Nov 2018 and first published on 19 Nov 2018


Article type: Paper
DOI: 10.1039/C8OB02469C
Citation: Org. Biomol. Chem., 2018,16, 9237-9242
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    Copper-catalyzed diastereoselective synthesis of β-boryl-α-quaternary carbon carboxylic esters

    Y. Zuo, Z. Zhong, Y. Fan, X. Li, X. Chen, Y. Chang, R. Song, X. Fu, A. Zhang and C. Zhong, Org. Biomol. Chem., 2018, 16, 9237
    DOI: 10.1039/C8OB02469C

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