AUTOMATIC ASSEMBLY OF SKELETON STRUCTURES .3. STEREOSELECTIVE SYNTHESIS, STEREOCHEMISTRY, AND CYCLIZATION OF HA,ALPHA'-DIOXY-ALPHA,ALPHA'-DI-TERT-BUTYLGLUTARIC ACID
Iv. Vystorop et al., AUTOMATIC ASSEMBLY OF SKELETON STRUCTURES .3. STEREOSELECTIVE SYNTHESIS, STEREOCHEMISTRY, AND CYCLIZATION OF HA,ALPHA'-DIOXY-ALPHA,ALPHA'-DI-TERT-BUTYLGLUTARIC ACID, Bulletin of the Russian Academy of Sciences, Division of Chemical Sciences, 41(7), 1992, pp. 1227-1234
Stereoselective synthesis of ha,alpha'-dioxy-alpha,alpha'-di-tert-buty
lglutaric acid hydroxyiminolactonitrile (3) was conducted by the react
ion of dipivaloylmethane with HCN in ether. The corresponding hydroxyl
acetonitrile (4) and amide (5), acid (6), and its ester (7), from whic
h dilactone (8) was synthesized with preparative yields, were obtained
from 3. Benzyl amide (9) was obtained by the reaction of 8 with BnNH2
. The iminolactone structure 3 of dipivaloylmethane bis-cyanohyrin, th
e cis-pseudo-a orientation of the functional substituents in 3-7 and 9
, and the structure of the dilactone 8 were confirmed by the H-1, C-13
NMR, IR and mass spectra.