Bibliographic Details
| Title: |
π-Face selective azaspirocyclization of ω-(methoxyphenyl)-N-methoxyalkylamides |
| Authors: |
Wardrop, Duncan J. wardropd@uic.edu, Burge, Matthew S.1, Zhang, Wenming1, Ortız, José A.1 |
| Source: |
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Mar2003, Vol. 44 Issue 12, p2587. 5p. |
| Subjects: |
Ring formation (Chemistry), Organic synthesis |
| Abstract: |
A novel method for the stereoselective preparation of 1-azaspiranes is described. Treatment of α- and β-substituted 3-(methoxyphenyl)-N-methoxypropionamides 1 with phenyliodine(III) bis(trifluoroacetate) initiates efficient azaspirocyclization, via a putative N-acylnitrenium ion intermediate, to provide cyclohexa-2,5 and 2,4-dienone spirolactams 8 and 11 with good π-facial selectivity. Furthermore, a preliminary study indicates that this strategy is also amenable to the preparation of 1-azaspiro[5.5]undeca-2,5-dienones. [Copyright &y& Elsevier] |
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| Database: |
Engineering Source |
