REGIOSELECTIVE ADDITION OF 1-TRIMETHYLSILYLOXY-1-METHOXY-1,3-DIENES TO ALDONITRONES CATALYZED BY TRIMETHYLSILYL TRIFLATE

Authors
CAMILETTI C DHAVALE DD DONATI F TROMBINI C
Citation
C. Camiletti et al., REGIOSELECTIVE ADDITION OF 1-TRIMETHYLSILYLOXY-1-METHOXY-1,3-DIENES TO ALDONITRONES CATALYZED BY TRIMETHYLSILYL TRIFLATE, Tetrahedron letters, 36(40), 1995, pp. 7293-7296
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
40
Year of publication
1995
Pages
7293 - 7296
Database
ISI
SICI code
0040-4039(1995)36:40<7293:RAO1T>2.0.ZU;2-S
Abstract
1-Trimethylsilyloxy-1-methoxy-1,3-dienes (3a-d) regioselectively add t o aldonitrones at -20 degrees C in dichloromethane in the presence of 10-20 % of trimethylsilyl triflate to give gamma-adducts in high yield s; on the other hand, 1-trimethylsilyloxy-1-methoxy-1,3-hexadiene (3e) displayes a reversed regiochemical preference affording the alpha-add uct as the major product.