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Copper-Catalyzed Borylative Aromatization of p-Quinone Methides: Enantioselective Synthesis of Dibenzylic Boronates.

ABSTRACT: In this report, we establish that DM-Segphos copper(I) complexes are efficient catalysts for the enantioselective borylation of para-quinone methides. This method provides straightforward access to chiral monobenzylic and dibenzylic boronic esters, with enantiomeric ratios up to 96:4, using a commercially available chiral phosphine. Standard manipulations of the C-B bond afford a variety of chiral diaryl derivatives.

SUBMITTER: Jarava-Barrera C

PROVIDER: S-EPMC4831668 | biostudies-literature | 2016 Jan

REPOSITORIES: biostudies-literature

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Copper-Catalyzed Borylative Aromatization of p-Quinone Methides: Enantioselective Synthesis of Dibenzylic Boronates.

Jarava-Barrera Carlos C Parra Alejandro A López Aurora A Cruz-Acosta Fabio F Collado-Sanz Daniel D Cárdenas Diego J DJ Tortosa Mariola M

ACS catalysis 20151211 1

In this report, we establish that DM-Segphos copper(I) complexes are efficient catalysts for the enantioselective borylation of para-quinone methides. This method provides straightforward access to chiral monobenzylic and dibenzylic boronic esters, with enantiomeric ratios up to 96:4, using a commercially available chiral phosphine. Standard manipulations of the C-B bond afford a variety of chiral diaryl derivatives. ...[more]

PMID: 27088045

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