Enzymatic synthesis of nonracemic inherently chiral calix[4]arenes by lipase-catalysed transesterification

Tetrahedron Letters

Volumn 39, Issue 13, 1998, Pages 1787-1790

  Browne, Julie K ^a   McKervey, M Anthony ^a   Pitarch, Miguel ^a   Russell, Julie A ^a   Millership, Jeffrey S ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; TRIACYLGLYCEROL LIPASE;

ACETYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; ENZYME MECHANISM; ESTERIFICATION; SYNTHESIS;

EID: 0032568264     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10865-6     Document Type: Article

References (13)

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9. 5. Pappalardo, S.; Caccamese, S.; Guinta, L. Tetrahedron Lett. 1991, 32, 7747-7750.
10. 1H NMR spectra, electrospray and FAB mass spectra were obtained for all new compounds.
11. 2Ar), 4.62 (1H, t, OH), 5.99 (1H, s, OH), 6.54 (1H, s, ArH), 6.55 (1H, s, ArH), 6.57 (1H, s, ArH), 6.58 (1H, s, ArH), 7.08 (2H, two overlapping s's, ArH), 7.18 (2H, two overlapping s's, ArH).
12. 8. St. Clair, N. L.; Navia, M. A. J. Am. Chem. Soc. 1992, 114, 7314-7316.
13. 9. Typical Experimental Procedure: To a solution of the corresponding alcohol (2 or 4) (100mg), dissolved in toluene was added vinyl acetate (15 eq.) and the lipase CLEC (30mg). The resulting mixture was stirred magnetically at room temperature until TLC (6:4 ethyl acetate:hexane) showed no further progress in the reaction. The lipase catalyst was filtered off and the filtrate concentrated to give the crude mixture of products. Purification by column chromatography (flash silica gel, 1:1 ethyl acetate:hexane) furnished the pure products.