Rate and enantioselectivity with complexes of activated substrates and simply modified cyclodextrins
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 8,p. 1121-1123
- https://doi.org/10.1039/p29870001121
Abstract
The rate of hydrolytic cleavage of a number of enantiomeric activated substrates, nitrophenyl esters or carbonates, was measured in the presence of some modified β-cyclodextrins: heptakis-[6-deoxy-6-(N-methylacetamido)]cyclohepta-amylose (9), heptakis-(2,6-di-O-methyl)cyclohepta-amylose (10), and heptakis-(2,3,6-tri-O-methyl)cyclohepta-amylose (11). In the presence of (9) the rate enhancements were considerably larger and enantioselectivities only slightly smaller than those observed with native β-cyclodextrin. With (10) and (11) inhibition was observed, the effects being substantially larger in the case of (10) than in that of the permethylated cyclodextrin (11), and enantioselectivity was virtually absent.Keywords
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