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Diastereoselective Alkylation of (Arene)tricarbonylchromium and Ferrocene Complexes Using a Chiral, C 2 ‐Symmetrical 1,2‐Diamine as Auxiliary
Author(s) -
Alexakis Alexandre,
Tomassini Axel,
Andrey Olivier,
Bernardinelli Gerald
Publication year - 2005
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.200400662
Subject(s) - chemistry , aminal , benzaldehyde , deprotonation , medicinal chemistry , electrophile , alkylation , diamine , ligand (biochemistry) , denticity , enantioselective synthesis , butyllithium , organic chemistry , stereochemistry , catalysis , crystal structure , ion , biochemistry , receptor
Abstract The aminal of (benzaldehyde)tricarbonylchromium and en‐antiopure bipyrrolidine undergoes diastereoselective ortho ‐metallation with butyllithium. Quenching with various electrophiles, followed by hydrolysis of the aminal, affords ortho ‐substituted (benzaldehyde)tricarbonylchromium compounds with high ee (91–99 %). When quenched with Ph 2 PCl, a new chiral P,N‐bidentate ligand is obtained, which shows efficiency in Pd‐ and Cu‐catalysed reactions. The aminal of ferrocenecarbaldehyde could also be formed, but the ortho ‐deprotonation occurs with only moderate diastereoselectivity (70 %). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)