BETA-OXY-ALPHA-DIAZO CARBONYL-COMPOUNDS .2. CONVERSION TO CHIRAL ALPHA-OXY-ALPHA'-DIAZO KETONES AND PHOTOCHEMICAL-REACTION

Citation
Fj. Lopezherrera et F. Sarabiagarcia, BETA-OXY-ALPHA-DIAZO CARBONYL-COMPOUNDS .2. CONVERSION TO CHIRAL ALPHA-OXY-ALPHA'-DIAZO KETONES AND PHOTOCHEMICAL-REACTION, Tetrahedron letters, 35(18), 1994, pp. 2929-2932
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404039
Volume
35
Issue
18
Year of publication
1994
Pages
2929 - 2932
Database
ISI
SICI code
0040-4039(1994)35:18<2929:BC.CTC>2.0.ZU;2-N
Abstract
Chiral beta-oxy-alpha-diazo methyl ketone was successfully converted t o alpha-oxy-alpha'-diazo ketone in three steps. The photochemical reac tion of this new diazo compound provides an improved synthesis of the 3-hydroxy-2-methyl carboxylate derivative 2 in threo relative configur ations via a Wolff rearrangement. The influence of the protective grou p on the stereochemical result of the photochemical reaction is discus sed.