ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
In order to developed a practical method for alkylating α-amino acids at the α- or β-carbon atom by intramolecular carbene C—H insertion, a series of diazoamides 3a-e was synthesized and subjected to rhodium(II) acetatecatalysed decomposition. The N-benzyl derivative 3a gave mainly the azetidinones 4a and 5a, resulting from a carbene C—H insertion into the N-benzyl group. The N-diphenylmethyl derivative 3c yielded, upon treatment with rhodium(II) acetate, the azetidinone 5c, the imine 6c, the cycloheptapyrrolidinone 7c as well as the desired pyrrolidinone 8c (12% yield) the latter resulting from an alkylation of the L-phenylalanine framework at the β-carbon atom.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19953370160
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