Csuk, Rene; Glaenzer, Brigitte I.; Hu, Zhong; Boese, Roland:

Double stereodifferentiating Dreiding-Schmidt reactions.

In: Tetrahedron (Tetrahedron), Jg. 50 (1994) ; Nr. 4, S. 1111-1124
ISSN: 0040-4020
Zeitschriftenaufsatz / Fach: Chemie
Spiroanellated carbohydrate-derived a-methylene-g-butyrolactones with an addnl. stereogenic center in the b-position of the anellated lactone ring and spiroanellated a-alkylidene-g-butyrolactones, e.g. I and II (R = Me, Et), were obtained in a stereoselective manner by Dreiding-Schmidt reactions of the deoxy-uloside III or of D-erythronolactone IV with the corresponding (Z) alkyl-2-bromomethyl-2-alkenoates, e.g., BrCH2C(CO2OEt):CHR in the presence of the highly reactive zinc-silver/graphite surface compd.