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Tutorial Review

Chem. Soc. Rev., 2009, 38, 3072 - 3081, DOI: 10.1039/b816701j


Domino reactions of rhodium(II) carbenoids for alkaloid synthesis

Albert Padwa


In this tutorial review, the rhodium(II)-catalyzed domino reactions of -diazo carbonyl compounds are summarized. The article will emphasize some of the more recent synthetic applications of the rhodium carbenoid cyclization/cycloaddition domino cascade for alkaloid synthesis. The many structurally diverse and highly successful examples of both oxa and azapolycyclic ring formation cited in this tutorial review clearly demonstrate that the domino cyclization/cycloaddition cascade of metallo carbenoids has evolved as an important strategy for the synthesis of nitrogen containing natural products.

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