DIASTEREOSELECTIVE CYCLOPROPANATION UTILIZING A NEW CHIRAL N,O-ACETALS PREPARED BY ELECTROCHEMICAL OXIDATION OF CARBAMATES

Authors
MATSUMURA Y ASANO T NAKAGIRI T ONOMURA O
Citation
Y. Matsumura et al., DIASTEREOSELECTIVE CYCLOPROPANATION UTILIZING A NEW CHIRAL N,O-ACETALS PREPARED BY ELECTROCHEMICAL OXIDATION OF CARBAMATES, Journal of the Chinese Chemical Society, 45(2), 1998, pp. 297-302
Citations number
19
Categorie Soggetti
Chemistry
Journal title
Journal of the Chinese Chemical Society → ACNP
ISSN journal
00094536
Volume
45
Issue
2
Year of publication
1998
Pages
297 - 302
Database
ISI
SICI code
0009-4536(1998)45:2<297:DCUANC>2.0.ZU;2-I
Abstract
A new chiral bicyclic tetrahydropyridine derivative was synthesized fr om L-lysine derivatives utilizing electrochemical oxidation as a key s tep. Allyl alcohols were incorporated into the tetrahydropyridine deri vative to afford N,O-acetals, and the reaction of the resulting N,O-ac etals with a carbenoid, which was generated from Et2Zn and CH2I3, yiel ded cyclopropanated products in moderate diastereoselectivities.