Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 1, Pages 97-102Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0517287
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Starting from natural proline, a practical chirospecific synthesis of spirocyclic beta-lactams of type 2 is described when a methylene moiety showing minimal steric demand is employed as a constraint element for adjusting the dihedral angle Psi(i + 1). Employing the concept of self-reproduction of chirality, C-formylation of the oxazolidinone 5 afforded the key intermediate 7 taking advantage of an intermediate protection of the bridging element as a vinyl moiety. NMR- and IR-based conformational studies clearly indicated that spiro-beta-lactams of type 2 can serve as efficient P-turn nucleators.
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