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Rhodium-catalyzed asymmetric hydroboration of ?,?-unsaturated amide derivatives: ?-borylated amides.

ABSTRACT: ?,?-Unsaturated amides in which the alkene moiety bears an aryl or heteroaryl substituent undergo regioselective rhodium-catalyzed ?-borylation by pinacolborane to afford chiral secondary benzylic boronic esters. The results contrast the ?-borylation of ?,?-unsaturated amides in which the disubstituted alkene moiety bears only alkyl substituents; the reversal in regiochemistry is coupled with a reversal in the sense of ?-facial selectivity.

SUBMITTER: Hoang GL 

PROVIDER: S-EPMC5975375 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives: δ-borylated amides.

Hoang G L GL   Zhang S S   Takacs J M JM  

Chemical communications (Cambridge, England) 20180501 38

γ,δ-Unsaturated amides in which the alkene moiety bears an aryl or heteroaryl substituent undergo regioselective rhodium-catalyzed δ-borylation by pinacolborane to afford chiral secondary benzylic boronic esters. The results contrast the γ-borylation of γ,δ-unsaturated amides in which the disubstituted alkene moiety bears only alkyl substituents; the reversal in regiochemistry is coupled with a reversal in the sense of π-facial selectivity. ...[more]

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