Bibliographic Details
| Title: |
Nucleophilic Carbene Catalyzed Synthesis of 1,2 Amino Alcohols Via Azidation of Epoxy Aldehydes. |
| Authors: |
Vora, Harit U.1, Moncecchi, Johannah R.1, Epstein, Oleg1, Rovis, Tomislav1 rovis@lamar.colostate.edu |
| Source: |
Journal of Organic Chemistry. 12/19/2008, Vol. 73 Issue 24, p9727-9731. 5p. 2 Charts. |
| Subjects: |
Organic chemistry, Chemical reactions, Aldehydes, Nucleophilic reactions, Amino acids, Nitrogen compounds |
| Abstract: |
We report herein a nucleophilic carbene catalyzed redox azidation of epoxyaldehydes. The intermediate β-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. [ABSTRACT FROM AUTHOR] |
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| Database: |
Engineering Source |
