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Nucleophilic carbene catalyzed synthesis of 1,2 amino alcohols via azidation of epoxy aldehydes.

ABSTRACT: We report herein a nucleophilic carbene catalyzed redox azidation of epoxyaldehydes. The intermediate beta-hydroxy acyl azides undergo thermal Curtius rearrangement followed by trapping with excess azide to form carbamoyl azides or, in a complementary sequence, by the hydroxy group to form oxazolidinones. Both products are formed in modest to good yields and diastereoselectivities. The use of an enantioenriched triazolium catalyst leads to modest asymmetric induction.

SUBMITTER: Vora HU

PROVIDER: S-EPMC4222516 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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Nucleophilic carbene catalyzed synthesis of 1,2 amino alcohols via azidation of epoxy aldehydes.

Vora Harit U HU Moncecchi Johannah R JR Epstein Oleg O Rovis Tomislav T

The Journal of organic chemistry 20081201 24

We report herein a nucleophilic carbene catalyzed redox azidation of epoxyaldehydes. The intermediate beta-hydroxy acyl azides undergo thermal Curtius rearrangement followed by trapping with excess azide to form carbamoyl azides or, in a complementary sequence, by the hydroxy group to form oxazolidinones. Both products are formed in modest to good yields and diastereoselectivities. The use of an enantioenriched triazolium catalyst leads to modest asymmetric induction. ...[more]

PMID: 18989930

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