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Chiral borane of layered α-Zirconium-N-(m-solfophenyl)-l-Valine-Phosphonate Methanphosphonate promoters for the asymmetric Mukaiyama Aldol reaction

Paper ID Volume ID Publish Year Pages File Format Full-Text
44334 46015 2007 6 PDF Available
Title
Chiral borane of layered α-Zirconium-N-(m-solfophenyl)-l-Valine-Phosphonate Methanphosphonate promoters for the asymmetric Mukaiyama Aldol reaction
Abstract

Several α-Zr[O3PC6H4SO2NHCH(CH(CH3)2)COOH)]2−x(O3PCH3)x·nH2O samples, containing chiral pendent groups, were prepared by allowing Zr fluoro complexes to decompose in the presence of N-(m-solfophenyl)-l(+)-Valine-phosphonic (PVal) and methanphosphonic (PMe) acids. The layered compounds were characterized by different techniques and left to react with BH3·THF reagent to obtain heterogeneous chiral oxazaborolidinone. These materials were found to be efficient catalysts of the typical asymmetric Mukaiyama Aldol reaction of 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene and benzaldehyde in CH2Cl2 and THF at 0 °C, with enantiomeric excess up to 50%.

Graphical abstractThe preparation of several layered α-Zirconium-N-(m-solfophenyl)-l(+)-Valine-Phosphonate Methanphosphonate samples and their use as heterogeneous chiral ligands for the in situ preparation of chiral oxazaborolidine catalysts for the asymmetric Mukaiyama Aldol reactions were reported. Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Heterogeneous asymmetric catalysis; Mukaiyama Aldol reactions; Zirconium phosphonate
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Chiral borane of layered α-Zirconium-N-(m-solfophenyl)-l-Valine-Phosphonate Methanphosphonate promoters for the asymmetric Mukaiyama Aldol reaction
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 326, Issue 1, 30 June 2007, Pages 100–105
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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Price was $35.95
You save - $31
Price after discount Only $4.95
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