Synthesis and characterisation of 5,11,17-tri-(tert-butyl)-23-dihydroxyboryl-25,26,27,28-tetrahydroxycalix[4]arene as a molecular scaffold for chiralboron Lewis acids

Authors
Hunter, R Koch, KR Verblun, B
Citation
R. Hunter et al., Synthesis and characterisation of 5,11,17-tri-(tert-butyl)-23-dihydroxyboryl-25,26,27,28-tetrahydroxycalix[4]arene as a molecular scaffold for chiralboron Lewis acids, S AFR J C-S, 51(4), 1998, pp. 200-206
Citations number
44
Categorie Soggetti
Chemistry
Journal title
SOUTH AFRICAN JOURNAL OF CHEMISTRY-SUID-AFRIKAANSE TYDSKRIF VIR CHEMIE
ISSN journal
03794350 → ACNP
Volume
51
Issue
4
Year of publication
1998
Pages
200 - 206
Database
ISI
SICI code
0379-4350(199812)51:4<200:SACO5>2.0.ZU;2-M
Abstract
The tri-(tert-butyl)calix[4]areneboronic acid 1 has been synthesised in sev en steps and 30% overall yield from p-(tert-butyl)calix[4]arene as a molecu lar scaffold for chiral Lewis acid production. The new bisphthalimido-1,2-d iol auxiliary 11 has been synthesised in four steps from (L)-diethyl tartra te and condensed with 1 to give the 'boriximide' derivative 8, which showed only marginal catalytic activity in the Diels-Alder reaction between metha crolein and cyclopentadiene.