DSM MonoPhos™ Family

Aldrich ChemFiles 2006, 6.4, 15.

Aldrich ChemFiles 2006, 6.4, 15.

Highly Efficient Privileged Ligands

Product Highlights

  • Superior enantiocontrol in numerous transformations
  • High activities at low catalyst loadings
  • Hydrogenations under low-pressure conditions
  • Applied in tandem reactions to yield valuable chiral organics

Feringa and co-workers have invented a diverse array of chiral, monodentate phosphoramidites based on the privileged BINOL platform.1 The MonoPhos™ family has exhibited high levels of enantiocontrol in synthetic transformations ranging from metal-catalyzed asymmetric 1,4-additions of organometallic reagents to allylic alkylations to desymmetrization of meso-cycloalkene oxides.2 Impressively, the (S)-N-benzyl-N-methyl-MonoPhos™ derivative has been utilized in highly selective hydrogenations of (E)-N-acylated dehydro-b-amino acid esters, affording the corresponding enantiopure b-amino acid derivatives.3 Sigma‑Aldrich, in collaboration with DSM, is pleased to offer a range of MonoPhos™ ligands for the research market.


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Materials

     

References

  1. Feringa, B. L. Acc. Chem. Res. 2000, 33, 346
  2. (a) Feringa, B. L. et al. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620 (b) Martina, S. L. X. et al. Tetrahedron Lett. 2005, 46, 7159 (c) Malda, H. et al. Org. Lett. 2001, 3, 1169 (d) Alexakis, A. et al. Chem. Commun. 2005, 2843 (e) Streiff, S. et al. Chem. Commun. 2005, 2957 (f) Bertozzi, F. et al. Org. Lett. 2000, 2, 933. (g) Ohmura, T. et al. J. Am. Chem. Soc. 2002, 124, 15164.
  3. (a) Pena, D. et al. J. Am. Chem. Soc. 2002, 124, 14552 (b) Van den Berg, M. et al. Adv. Synth. Catal. 2003, 345, 308.

MonoPhos™ family ligands are sold under license from DSM for research purposes only. Patent WO 0204466 applies.

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