Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 24, Pages 9727-9731Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo8020055
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Funding
- NIGMS [GM72586]
- Herman Frasch Foundation
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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.
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