Unexpected 1,3-oxazolidine formation in the attempted oxidation of N-aryl-N-methyl substituted β-amino alcohols using pyridinium dichromate
✍ Scribed by Jari T. Yli-Kauhaluoma; Curtis W. Harwig; Paul Wentworth Jr.; Kim D. Janda
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 279 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
1,3-Oxazolidines were obtained from the reaction of N-methyl substituted &amino alcohols with pyridinium dichromate in dichloromethane.
A single electron transfer mechanism. SET, is proposed to account for the formation of the 1,3-oxazolidines.
📜 SIMILAR VOLUMES
Nonstabilized azomethme ylides generated from the various B-amino alcohols N-oxides 13,17, 23 and 24 undergo [3+2] cycloadditron reactions with unactivated alkenes to afford the corresponding pyrrolidines 14a-g, 18a-g, 25 and 27 in moderate to good yields. These compounds are precursors of NH pyrrol
At room temperature, the presence of hydrogen and catalytic amounts of Pd/C induced the formation of 1,3-oxazolidines from nitriles and 1,2-amino alcohols. The subsequent reductive cleavage of the NC-O bond of lhese heterocycles occurred under the same conditions. Thus, this methodology provides a n