BETA-OXY-ALPHA-DIAZO CARBONYL-COMPOUNDS .4. REACTION WITH TRIETHYL BORANE - THE INFLUENCE OF THE OXY GROUP IN THE REGIO-CONTROLLED AND STEREO-CONTROLLED ALKYLATION ON THE DIAZO CARBON

Authors
LOPEZHERRERA FJ SARABIAGARCIA F
Citation
Fj. Lopezherrera et F. Sarabiagarcia, BETA-OXY-ALPHA-DIAZO CARBONYL-COMPOUNDS .4. REACTION WITH TRIETHYL BORANE - THE INFLUENCE OF THE OXY GROUP IN THE REGIO-CONTROLLED AND STEREO-CONTROLLED ALKYLATION ON THE DIAZO CARBON, Tetrahedron letters, 36(16), 1995, pp. 2851-2854
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
16
Year of publication
1995
Pages
2851 - 2854
Database
ISI
SICI code
0040-4039(1995)36:16<2851:BC.RWT>2.0.ZU;2-0
Abstract
The reactions of chiral beta-oxy-alpha-diazocarbonyl compounds with tr iethylborane were studied. The results of the reactions depend on the particular group used to protect the beta-hydroxyl function. Thus, hin dered protecting groups lead to N-alkylation of the diazo compound. On the other hand, the product with a free hydroxyl group, undergoes C-a lkylation in a good yield with full stereoselectivity.