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Issue 44, 2020
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Consecutive borylcupration/C–C coupling of γ-alkenyl aldehydes towards diastereoselective 2-(borylmethyl)cycloalkanols

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Abstract

Copper(I) catalyzes the borylative cyclization of γ-alkenyl aldehydes through chemo- and regioselective addition of Cu–B to C[double bond, length as m-dash]C and concomitant intramolecular 1,2-addition of Cu–C on C[double bond, length as m-dash]O. The products are formed in an exclusive diastereoselective manner and computational analysis identifies the key points for the observed chemo- and diastereoselectivity.

Graphical abstract: Consecutive borylcupration/C–C coupling of γ-alkenyl aldehydes towards diastereoselective 2-(borylmethyl)cycloalkanols

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Supplementary files

Article information


Submitted
30 Mar 2020
Accepted
13 Apr 2020
First published
13 Apr 2020

Chem. Commun., 2020,56, 5973-5976
Article type
Communication

Consecutive borylcupration/C–C coupling of γ-alkenyl aldehydes towards diastereoselective 2-(borylmethyl)cycloalkanols

R. J. Maza, J. Royes, J. J. Carbó and E. Fernández, Chem. Commun., 2020, 56, 5973
DOI: 10.1039/D0CC02263B

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