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Stereoselective Tandem Bis-Electrophile Couplings of Diborylmethane.

ABSTRACT: A copper-catalyzed three-component linchpin coupling method for the stereoselective union of readily available epoxides and allyl electrophiles is disclosed. Transformations employ [B(pin)]2-methane as a conjunctive reagent, resulting in the formation of two C-C bonds at a single carbon center bearing a C(sp3) organoboron functional group. Products are obtained in 42-99% yield, and up to >20:1 dr. The utility of the approach is highlighted by stereospecific transformations entailing allylation, tandem cross coupling, and application to the synthesis 1,3-polyol motifs.

SUBMITTER: Murray SA

PROVIDER: S-EPMC5711522 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Stereoselective Tandem Bis-Electrophile Couplings of Diborylmethane.

Murray Stephanie A SA Liang Michael Z MZ Meek Simon J SJ

Journal of the American Chemical Society 20170927 40

A copper-catalyzed three-component linchpin coupling method for the stereoselective union of readily available epoxides and allyl electrophiles is disclosed. Transformations employ [B(pin)]<sub>2</sub>-methane as a conjunctive reagent, resulting in the formation of two C-C bonds at a single carbon center bearing a C(sp<sup>3</sup>) organoboron functional group. Products are obtained in 42-99% yield, and up to >20:1 dr. The utility of the approach is highlighted by stereospecific transformations ...[more]

PMID: 28934852

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