Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 18, Pages 3861-3870Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201400563
Keywords
asymmetric synthesis; azomethine ylides; dipolar cycloaddition; phosphoramidites; silver
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Funding
- Spanish Ministerio de Ciencia e Innovacion (MICINN) [CSD2007-00006, CTQ2010-20387]
- FEDER
- Generalitat Valenciana [PROMETEO/2009/039abd PROMETEOII/2014/017]
- University of Alicante
- MICINN
- FEDER [CSD2007-00006, CTQ2010-16959/BQU]
- University of the Basque Country (UPV/EHU) [UFI11/22 QOSYC]
- Basque Government (GV/EJ) [IT-324-07]
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Chiral complexes formed by privileged phosphoramidites and silver triflate or silver benzoate are excellent catalysts for the general 1,3-dipolar cycloaddition between azomethine ylides generated from alpha-amino acid-derived imino esters and nitroalkenes affording with high dr the exo-cycloadducts 4,5-trans-2,5-cis-4-nitroprolinates in high ee at room temperature. In general, better results are obtained using silver rather than copper(II) complexes. In many cases the exo-cycloadducts can be obtained in enantiomerically pure form just after simple recrystallization. The mechanism and the justification of the experimentally observed stereodiscrimination of the process are supported by DFT calculations. These enantiomerically enriched exo-nitroprolinates can be used as reagents for the synthesis of nitropiperidines, by ester reduction and ring expansion, which are inhibitors of farnesyltransferase.
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