Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2008, Issue 30, Pages 5055-5066Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800650
Keywords
Asymmetric catalysis; P,N ligands; Palladium; Atropisomerism; Biaryl compounds
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Funding
- European Community's Sixth Framework Programme [FP6-505267-1]
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An expedient, seven-step synthesis of two new members of the Quinazolinap, hgand family, 2-cyclobutyl- and 2-(1-adamantyl)-Quinazohnaps, has been developed. The racemic ligands have been efficiently resolved by fractional crystallization of their diastereomeric palladacycle complexes. The enantioenriched ligands provide good levels of enantioselection (ee's up to 89%) in a prototypical Pd-II-catalyzed allylic alkylation reaction. 2-Cyclobutyl-Quinazohnap has been further functionalized at the 2-position via metalation with a superbase followed by reaction with a range of electrophiles. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
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