EFFICIENT PREPARATION AND RESOLUTION OF TRANS-1,2-CYCLOBUTANEDICARBOXYLIC ACID AND SOME OF ITS DERIVATIVES

Authors
BRUNET JJ HERBOWSKI A NEIBECKER D
Citation
Jj. Brunet et al., EFFICIENT PREPARATION AND RESOLUTION OF TRANS-1,2-CYCLOBUTANEDICARBOXYLIC ACID AND SOME OF ITS DERIVATIVES, Synthetic communications, 26(3), 1996, pp. 483-493
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
26
Issue
3
Year of publication
1996
Pages
483 - 493
Database
ISI
SICI code
0039-7911(1996)26:3<483:EPAROT>2.0.ZU;2-G
Abstract
The readily available cis/trans mixture of 1,2-cyclobutanedicarboxylic acid undergoes a quantitative isomerization in 12N HCl to the trans-d iacid (as monitored by NMR spectroscopy). The latter is resolved to th e (+)- and (-)-trans-diacids by modified literature and patented metho ds. The synthesis of the (S,S)-(-)-trans-diol and (S,S)-(+)-trans-dito sylate from the (S,S)-(+)-trans-diacid is also reported.