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

Published inEuropean journal of organic chemistry, vol. 2005, no. 7, p. 1332-1339
Publication date2005
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
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. doi: 10.1002/ejoc.200400662
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ISSN of the journal1099-0690
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