LIPASE-CATALYZED KINETIC RESOLUTION OF CYCLOBUTYLMETHANOLS AND DETERMINATION OF ABSOLUTE STEREOCHEMISTRY BY X-RAY-ANALYSIS

Authors
NEMOTO H MIYATA J FUKUMOTO K EHARA H HARADA N UEKUSA H OHASHI Y
Citation
H. Nemoto et al., LIPASE-CATALYZED KINETIC RESOLUTION OF CYCLOBUTYLMETHANOLS AND DETERMINATION OF ABSOLUTE STEREOCHEMISTRY BY X-RAY-ANALYSIS, Enantiomer, 2(2), 1997, pp. 127-131
Citations number
25
Categorie Soggetti
Chemistry,"Chemistry Inorganic & Nuclear",Biology
Journal title
Enantiomer → ACNP
ISSN journal
10242430
Volume
2
Issue
2
Year of publication
1997
Pages
127 - 131
Database
ISI
SICI code
1024-2430(1997)2:2<127:LKROCA>2.0.ZU;2-A
Abstract
The transesterification of 2-(hydroxymethyl) -2-phenyl-cyclobutanone ( 4) and 3-methoxybicyclo [4.2.0]octal,3,5-triene-7-methanol (5) with vi nyl acetate catalyzed by lipase in several solvent systems was examine d and high (99.5%) enantioselectivity was observed for 5 in CHCl3. The absolute stereochemistry of alcohol (+)-5 has been unambiguously dete rmined to be R by X-ray analysis of derivative 11 containing a chiral auxiliary of known absolute configuration, although compound 11 was ve ry sensitive to X-ray treatment.