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
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.