The enantiomerically pure crystalline α,β-unsaturated γ-lactams 4 and 5 have been synthesized by utilizing 2,3-O-isopropylidene-D-glyceraldehyde (3) as chiral source and novel N-tert-butoxycarbonyl-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as four carbon homologative reagent. Unsaturated lactam 4 has been selectively elaborated into hydroxylated pyrrolidinones 7, 8, and 11 by stereocontrolled procedures involving conjugate addition of organocuprates, cis-dihydroxylation, and α-alkylation via hydrogenation and enulate formation. The absolute stereochemistries of 4 and 5 have been secured by single crystal X-ray analyses. © 1992.

Homochiral α,β-unsaturated γ-lactams: Versatile templates / Rassu, Gloria; Casiraghi, Giovanni; Spanu, Pietro; Pinna, Luigi; Fava, Giovanna Gasparri; Ferrari, Marisa Belicchi; Pelosi, Giorgio. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 3:8(1992), pp. 1035-1048. [10.1016/S0957-4166(00)86037-1]

Homochiral α,β-unsaturated γ-lactams: Versatile templates

CASIRAGHI, Giovanni;PELOSI, Giorgio
1992

Abstract

The enantiomerically pure crystalline α,β-unsaturated γ-lactams 4 and 5 have been synthesized by utilizing 2,3-O-isopropylidene-D-glyceraldehyde (3) as chiral source and novel N-tert-butoxycarbonyl-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as four carbon homologative reagent. Unsaturated lactam 4 has been selectively elaborated into hydroxylated pyrrolidinones 7, 8, and 11 by stereocontrolled procedures involving conjugate addition of organocuprates, cis-dihydroxylation, and α-alkylation via hydrogenation and enulate formation. The absolute stereochemistries of 4 and 5 have been secured by single crystal X-ray analyses. © 1992.
Homochiral α,β-unsaturated γ-lactams: Versatile templates / Rassu, Gloria; Casiraghi, Giovanni; Spanu, Pietro; Pinna, Luigi; Fava, Giovanna Gasparri; Ferrari, Marisa Belicchi; Pelosi, Giorgio. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 3:8(1992), pp. 1035-1048. [10.1016/S0957-4166(00)86037-1]
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11381/2823046
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