http://www.cnr.it/ontology/cnr/individuo/prodotto/ID47815
Asymmetric synthesis of 1,3-thiazolidine-derived spiro-beta-lactams via a Staudinger reaction between chiral ketenes and imines (Articolo in rivista)
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- Asymmetric synthesis of 1,3-thiazolidine-derived spiro-beta-lactams via a Staudinger reaction between chiral ketenes and imines (Articolo in rivista) (literal)
- Anno
- 2005-01-01T00:00:00+01:00 (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
- 10.1016/j.tetasy.2005.08.054 (literal)
- Alternative label
Cremonesi G., Dalla Croce P., Fontana F., Forni A., La Rosa C. (2005)
Asymmetric synthesis of 1,3-thiazolidine-derived spiro-beta-lactams via a Staudinger reaction between chiral ketenes and imines
in Tetrahedron: asymmetry (Print); PERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD (Regno Unito)
(literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
- Cremonesi G., Dalla Croce P., Fontana F., Forni A., La Rosa C. (literal)
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- IF 2005: 2.429;
SJR 2005: Inorganic Chemistry, Q1 (literal)
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- http://www.sciencedirect.com.pros.lib.unimi.it/science/article/pii/S0957416605007482 (literal)
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- ISI Web of Science (WOS) (literal)
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- Istituto di Chimica Organica 'A. Marchesini', Facolta' di Farmacia, V. Venezian 21, I-20133 Milano, Italy;
Dipartimento di Chimica Organica e Industriale and C.N.R.-I.S.T.M., V. Venezian 21, I-20133 Milano, Italy;
C.N.R.-I.S.T.M., V. Golgi, 19, I-20133 Milano, Italy (literal)
- Titolo
- Asymmetric synthesis of 1,3-thiazolidine-derived spiro-beta-lactams via a Staudinger reaction between chiral ketenes and imines (literal)
- Abstract
- Enantiomerically pure 1,3-thiazolidine-derived spiro-beta-lactams were stereoselectively synthesised by means of a Staudinger ketene-imine reaction starting from optically active N-Boc-1,3-thiazolidine-2-carboxylic acid derivatives and imines. The reactions were stereoselective and afforded spiro-beta-lactams with a relative trans-configuration. The absolute configuration of the new stereocentres was assigned on the basis of the well-accepted mechanism and confirmed by means of the X-ray crystal structure analysis. The spiro-beta-lactams were transformed into enantiomerically pure chiral monocyclic beta-lactams by opening the thiazolidine ring and recovering the chiral auxiliary. (literal)
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