Diastereoselective alkylation of (Arene)tricarbonyl-chromium and ferrocene complexes using a chiral C2-symmetrical 1,2 diamine as auxiliary

Alexakis, Alexandre; Tomassini, Axel; Andrey, Olivier; Bernardinelli, Gérald Hugues

doi:10.1002/ejoc.200400662

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Title		Diastereoselective alkylation of (Arene)tricarbonyl-chromium and ferrocene complexes using a chiral C2-symmetrical 1,2 diamine as auxiliary
Authors		Alexakis, Alexandre Tomassini, Axel Andrey, Olivier Bernardinelli, Gérald Hugues
Published in		European Journal of Organic Chemistry. 2005, vol. 2005, no. 7, p. 1332-1339
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 Ph2PCl, 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 %).
Keywords		Aminals — Chromium — Diamines — Homogeneous catalysis — Planar chirality
Identifiers		DOI: 10.1002/ejoc.200400662
Full text		Article (Published version) - Limited access to UNIGE
Structures		Faculté des sciences / Section de chimie et biochimie / Département de chimie organique
Citation (ISO format)		ALEXAKIS, Alexandre et al. Diastereoselective alkylation of (Arene)tricarbonyl-chromium and ferrocene complexes using a chiral C2-symmetrical 1,2 diamine as auxiliary. In: European Journal of Organic Chemistry, 2005, vol. 2005, n° 7, p. 1332-1339. https://archive-ouverte.unige.ch/unige:8033