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Combining NHC-Cu and Bronsted base catalysis: enantioselective allylic substitution/conjugate additions with alkynylaluminum reagents and stereospecific isomerization of the products to trisubstituted allenes.

ABSTRACT: All-catalytic route to trisubstituted allenes: The first examples of catalytic enantioselective allylic substitution reactions that involve alkyne-based nucleophiles and lead to products having tertiary stereogenic centers are followed by an exceptionally stereospecific amine-catalyzed isomerization to trisubstituted allenes (see picture; NHC = N-heterocyclic carbene).

SUBMITTER: Dabrowski JA

PROVIDER: S-EPMC3804904 | biostudies-other | 2013 Jul

REPOSITORIES: biostudies-other

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Combining NHC-Cu and Brønsted base catalysis: enantioselective allylic substitution/conjugate additions with alkynylaluminum reagents and stereospecific isomerization of the products to trisubstituted allenes.

Dabrowski Jennifer A JA Haeffner Fredrik F Hoveyda Amir H AH

Angewandte Chemie (International ed. in English) 20130618 30

All-catalytic route to trisubstituted allenes: The first examples of catalytic enantioselective allylic substitution reactions that involve alkyne-based nucleophiles and lead to products having tertiary stereogenic centers are followed by an exceptionally stereospecific amine-catalyzed isomerization to trisubstituted allenes (see picture; NHC = N-heterocyclic carbene). ...[more]

PMID: 23864395

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