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Synthesis, Resolution, and Application of Cyclobutyl‐ and Adamantyl‐Quinazolinap Ligands
Author(s) -
Fekner Tomasz,
MüllerBunz Helge,
Guiry Patrick J.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800650
Subject(s) - chemistry , metalation , electrophile , superbase , tsuji–trost reaction , diastereomer , alkylation , ligand (biochemistry) , stereochemistry , allylic rearrangement , hydroamination , reaction conditions , combinatorial chemistry , organic chemistry , catalysis , receptor , biochemistry
An expedient, seven‐step synthesis of two new members of the Quinazolinap ligand family, 2‐cyclobutyl‐ and 2‐(1‐adamantyl)‐Quinazolinaps, 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‐Quinazolinap has been further functionalized at the 2‐position via metalation with a superbase followed by reaction with a range of electrophiles. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)