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Enantioselective rhodium-catalyzed [4+2+2] cycloaddition of dienyl isocyanates for the synthesis of bicyclic azocine rings.

ABSTRACT: A highly enantioselective rhodium-catalyzed [4+2+2] cycloaddition of terminal alkynes and dienyl isocyanates has been developed. The cycloaddition provides a rapid entry to highly functionalized and enantioenriched bicyclic azocines. This reaction represents the first [4+2+2] cycloaddition strategy to construct nitrogen-containing eight-membered rings.

SUBMITTER: Yu RT

PROVIDER: S-EPMC2774260 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Enantioselective rhodium-catalyzed [4+2+2] cycloaddition of dienyl isocyanates for the synthesis of bicyclic azocine rings.

Yu Robert T RT Friedman Rebecca Keller RK Rovis Tomislav T

Journal of the American Chemical Society 20090901 37

A highly enantioselective rhodium-catalyzed [4+2+2] cycloaddition of terminal alkynes and dienyl isocyanates has been developed. The cycloaddition provides a rapid entry to highly functionalized and enantioenriched bicyclic azocines. This reaction represents the first [4+2+2] cycloaddition strategy to construct nitrogen-containing eight-membered rings. ...[more]

PMID: 19711950

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