Diastereoselective Synthesis of Highly Constrained Spiro‐β‐Lactams by the Staudinger Reaction Using an Unsymmetrical Bicyclic Ketene
作者： Andrea Trabocchi , Claudia Lalli , Francesco Guarna , Antonio Guarna
关键词:
摘要: A rigid bicyclic ketene was used to generate highly constrained polycyclic spiro-β-lactams through the Staudinger reaction. Depending on imine component, high diastereoselectivity observed in process, leading mainly cis diastereoisomer case of aromatic imines. This results from an anti addition ketene, followed by a conrotatory ring closure which heteroatom at 6-position scaffold rotates outward because torquoelectronic effects.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
sci-hub.se 参考文章(56)
William L. Scott, Jordi Alsina, Joseph H. Kennedy, Martin J. O'Donnell, Solid-phase synthesis of constrained terminal and internal lactam peptidomimetics Organic Letters. ,vol. 6, pp. 1629- 1632 ,(2004) , 10.1021/OL049547Z
Benito Alcaide, Pedro Almendros, Raquel Rodríguez-Acebes, Pd–Cu Bimetallic Catalyzed Domino Cyclization of α‐Allenols Followed by a Coupling Reaction: New Sequence Leading to Functionalized Spirolactams Chemistry: A European Journal. ,vol. 11, pp. 5708- 5712 ,(2005) , 10.1002/CHEM.200500228
Stephen Hanessian, Grant McNaughton-Smith, Henry-Georges Lombart, William D. Lubell, Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics Tetrahedron. ,vol. 53, pp. 12789- 12854 ,(1997) , 10.1016/S0040-4020(97)00476-6
Andrea Trabocchi, Nicoletta Cini, Gloria Menchi, Antonio Guarna, A new bicyclic proline-mimetic amino acid Tetrahedron Letters. ,vol. 44, pp. 3489- 3492 ,(2003) , 10.1016/S0040-4039(03)00663-4
Carina M. L. Delpiccolo, M. Amelia Fraga, Ernesto G. Mata, An efficient, stereoselective solid-phase synthesis of beta-lactams using Mukaiyama's salt for the Staudinger reaction. ACS Combinatorial Science. ,vol. 5, pp. 208- 210 ,(2003) , 10.1021/CC020107D
Piero Dalla Croce, Raffaella Ferraccioli, Concetta La Rosa, Reaction of mesoionic compounds deriving from cyclic N-acyl-α-aminoacids with N-(phenylmethylene)benzenesulfonamide Tetrahedron. ,vol. 55, pp. 201- 210 ,(1999) , 10.1016/S0040-4020(98)01026-6
Lino Colombo, Marcello Di Giacomo, Valerio Vinci, Matteo Colombo, Leonardo Manzoni, Carlo Scolastico, Synthesis of new bicyclic lactam peptidomimetics by ring-closing metathesis reactions Tetrahedron. ,vol. 59, pp. 4501- 4513 ,(2003) , 10.1016/S0040-4020(03)00684-7
Iwao Ojima, Recent Advances in the .beta.-Lactam Synthon Method Accounts of Chemical Research. ,vol. 28, pp. 383- 389 ,(1995) , 10.1021/AR00057A004
Tobias Hoffmann, Reiner Waibel, Peter Gmeiner, A general approach to dehydro-Freidinger lactams: ex-chiral pool synthesis and spectroscopic evaluation as potential reverse turn inducers. Journal of Organic Chemistry. ,vol. 68, pp. 62- 69 ,(2003) , 10.1021/JO0261653
A Macias, Unusual rearrangement of spiro $beta;-lactams to 1,4-diazabicyclo64,4,09decanes and 1,4-diazabicyclo64,3,09nonanes. Synthesis of conformationally restricted $sigma;-receptor ligands Tetrahedron Letters. ,vol. 45, pp. 4657- 4660 ,(2004) , 10.1016/S0040-4039(04)00901-3