US EPA

7695232 

Journal Article 

Studies on double hydrolytic transformation of chiral cyclopropane derivatives 

Zhang, XL; Huang, HH; Chen, QH; , 

2003 

1 

Youji Huaxue / Chinese Journal of Organic Chemistry
ISSN: 0253-2786 

SCIENCE PRESS 

BEIJING 

23 

1 

76-80 

Chinese 

WOS:000181185700012 

The functionalized spiro-cyclopropane derivatives containing four stereogenic centers 4 were undergone stereoselective double hydrolytic transformation of the auxiliary groups in the presence of acetone/12% HCl to afford the crude products 5. After separation though column chromatography and recrystallization, the pure chiral cyclopropane/bis-hemiacetal derivatives, spiro-[1-bromo-4-hydroxy-5-oxa-6-oxo-bicyclo-[3.1.0]-hexane-2, 2'-( 3'-nucleophilic group-4'-hydroxy-butyrolactone) 1 (5), were obtained in 65% similar to 79% yields with ee greater than or equal to 98%. The novel chiral compounds 5a similar to 5e were identified on the basis of their analytical data and spectroscopic data, such as UV, IR, H-1 NMR, C-13 NMR, MS, elementary analysis and X-ray crystallography analysis. 

Absolute configuration; Chiral cyclopropane/bis-hemiacetals derivative; Double hydrolytic transformation; Stereochemistry