ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Preparations of dimethyl (1RS,2SR,4RS,5SR,6SR,7RS)- and dimethyl (1 RS,2SR,4RS,5SR,6RS,7SR)-8-oxa-3-azatricyclo[3;2.1.024] octane-6,7-dicarboxylate 15 and18, resp.) and of their N-(tert-butyloxy)carbonyl (14, 17) and V-benzoyl (16, 19) derivatives are described. While treatment with nucleophilic acids (HCl, HBr. AcOH) of the exo, exo-diesters 14 and 16 gave the corresponding products 23-27 of aziridine trans -addition, the exo, endo -diesters 17 and 19 led to the corresponding amino-lactones 63 (methyl (1RS,2RS,3SR,6RS,7SR,9RS)-2-{[(tert-butyloxy)carbonyl] amino}-5-oxo-4,8-dioxatricyclo[4.2.1.0 37] nonane-9-carboxylate) and 64 (methyl (1RS,2RS,3SR,6RS,7SR,9SR)-2-(benzoylamino)-5-oxo-4,8-dioxatricyclo[4.2.1.0 3′7] (nonane-9-carboxylate). Under non-nucleophilic acidic conditions, the N-benzoylaziridine 16 was rearranged quantitatively into dimethyl (1RS,2SR,26SR,67SR,7SR,8SR,9SR)-4-phenyl-5,10-dioxa-3-azatricyclo[4.3.1.02′7] dec-3-ene-8,9-dicarboxylate(31), and 19 into dimethyl (1RS,2SR,26SR,67SR,7SR,8SR,9SR)-4-phenyl-3,10-dioxa-5-azatricyclo [5.2.1.02′6] dec-4-ene-8,9-di-carboxylate (65). Possible mechanisms of these highly selective reactions and rearrangements are discussed.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19900730316
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