Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 1, Pages 146-151Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800598
Keywords
Phosphanes; Asymmetric catalysis; [3+2] Cyclisations; Allenes; Imines
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Funding
- Agence Nationale de la Recherche (ANR)
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The use of binaphthophosphepine la as a catalyst for the [3+2] cyclisation between allenoates or 2-butynoates and imines was investigated. The effects of the imine protecting group on both the catalytic activity and enantioselectivity were-determined by comparing the behaviour of N-tosyl- and N-DPP-imines. The N-DPP-imines displayed lower reactivity, but afforded the desired pyrrolines in higher enantiomeric excess (73-92% ee). The DPP protecting group was removed from the final pyrrolines under mild conditions to afford the corresponding secondary amines. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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