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Abstract
The condensation of phenylaziridines ( 3a/3b) with 3-cyclopentenylsilane ( 4) in presence of BF 3.Et 2O yielded amino-cyclopentenyl adducts ( 5a–8a) and ( 5b–8b). Heterocyclisation of the ω-amino-olefins assisted by Pd(OAc) 2 afforded the azabicyclo adducts 2a/2′a and 2b/2′b. Oxidation of the internal double bond, followed by epimerization at C(2) was realized by KH in presence of 18-crown-6 yielding 11, the fully protected phenylkainic acid.
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