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7448497 
Journal Article 
Diastereoselection of the addition of silyloxyfurans to five-, six- and seven-membered N-acyliminium ions 
de Oliveira, MDF; Santos, LS; Pilli, RA 
2001 
1 
Tetrahedron Letters
ISSN: 0040-4039
EISSN: 1873-3581 
PERGAMON-ELSEVIER SCIENCE LTD 
OXFORD 
42 
40 
6995-6997 
English 
WOS:000171212000005 
The addition of silyloxyfuran 1a to five-, six- and seven-membered N-acyliminium ions 2 afforded threo-3 as the major isomers (the structures of 3a, 3g and 3m were determined by X-ray analysis). The diastereoisomeric ratio increased with bulkier carbamate groups (Boc>Cbz>CO2Me) with the five- and seven-membered N-acyliminium ions more selective than the six-membered ones. However. erythro-4 isomers predominated when 5-methylsilyloxyfuran 1b was employed (the structures were determined by NOE studies on the corresponding bicyclic lactams 6a.b and 7a,b) and the formation or regioisomer 5 was observed for N-acyliminium ions with Boc (seven-membered series) and Cbz (six- and seven-membered series) groups. (C) 2001 Elsevier Science Ltd. All rights reserved. 
5 methylsilyloxyfuran; carbamic acid; furan derivative; iminium ion; ion; lactam derivative; silyloxyfuran derivative; unclassified drug; article; chemical reaction; chemical structure; diastereoisomer; reaction analysis; stereochemistry; stereoisomerism; X ray analysis; Staphylococcus phage 3A 
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