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Structurally Diverse Second‐Generation [2.2]Paracyclophane Ketimines with Planar and Central Chirality: Syntheses, Structural Determination, and Evaluation for Asymmetric Catalysis
Author(s) -
Lauterwasser Frank,
Nieger Martin,
Mansikkamäki Heidi,
Nättinen Kalle,
Bräse Stefan
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500146
Subject(s) - diethylzinc , planar chirality , chirality (physics) , catalysis , chemistry , enantioselective synthesis , absolute configuration , planar , stereochemistry , combinatorial chemistry , organic chemistry , chiral symmetry , physics , computer science , computer graphics (images) , quantum mechanics , quark , nambu–jona lasinio model
A set of 20 novel [2.2]paracyclophane ketimines with planar and central chirality has been synthesized from enantiomerically pure and racemic 5‐acyl‐4‐hydroxy[2.2]paracyclophane and α‐branched chiral amines. Their X‐ray structures were determined to elucidate the three‐dimensional structures and the absolute configuration. The ketimines were used as catalysts in the asymmetric 1,2‐addition reactions of diethylzinc with substituted benzaldehydes to furnish chiral alcohols in up to 95 % ee .