Cycloaddition of 5-substituted 1- pyrroline 1-oxide and conversion of the nitrone cycloadducts into cis-and trans- 2,5-disubstituted pyrrolidines
1993; Elsevier BV; Volume: 49; Issue: 20 Linguagem: Inglês
10.1016/s0040-4020(01)85751-3
ISSN1464-5416
AutoresShaikh A. Ali, Mohammed I.M. Wazeer,
Tópico(s)Chemical Synthesis and Analysis
ResumoA study of the regiochemical behaviour of the oxidation of 2-substituted-1-hydroxypyrrolidines (2) being to aldo- and kito-nitrones has been carried out. The mechanism of the peracid induced ring opening reaction of isoxazolidines (5) is now firmly established. Second cycloaddition reaction of 5-substituted 1- pyrroline 1-oxide (6) provides an efficient and stereoselective entry into the trans- (24) as well as cis-2,5- disubstituted pyrrolidines (28).
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