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EnglishThe p-nitrobenzoates I were stereospecifically transformed with AgOAc-AcOH into the penam derivs. II. Oxidn. of II yielded the (S)- and (R)-sulfoxides. The (R)-sulfoxide of the α-acetoxymethyl isomer was thermally converted into the (S)-sulfoxide of the β-acetoxymethyl isomer. The configurations of II and the sulfoxides were assigned on the basis of 1H NMR studies and mechanistic considerations. The exclusive formation of II from I implies the intermediate formation of the diastereoisomeric α- and β-episulfonium ions, which undergo regiospecific attack of the nucleophile on the methylene carbon.
| Autori interni: | |
| Autori: | A. BALSAMO; B. MACCHIA; F. MACCHIA P. SCATENA; P. DOMIANO; ROSSELLO A |
| Titolo: | Conversion reactions of cepham into penam systems. A route to determine the relative configurations of two diastereoisomeric 3-bromo-4-methoxycepham derivatives |
| Anno del prodotto: | 1986 |
| Digital Object Identifier (DOI): | 10.1021/jo00354a028 |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
File in questo prodotto:
http://hdl.handle.net/11568/204694
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