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Solvias launches chiral phosphoric acids (CPA)

Solvias is expanding its catalyst and ligand portfolio with chiral Brønsted acid (organo)catalysts. Due to new innovative syntheses, these chiral binaphthol-based phosphoric acids are offered at very competitive prices in up to multi-100 g quantities under license of Toagosei.
These well-established chiral acids can be employed at industrially benign catalyst loadings in more than 80 different reactions.

Chiral BINOL-derived Brønsted acids allow for the formation of C−C, C−H and C−X bonds in a highly enantioselective fashion. Thus, CPAs represent a useful alternative to metal catalysis and chiral auxiliaries. In contrast to other organocatalysts CPAs can be employed at relatively low catalyst loadings and both enantiomers are available. Furthermore CPAs can act as chiral anions in asymmetric counterion directed catalysis and as ligands in transition metal-catalyzed transformations (Lewis acid catalysis, non-Lewis acid catalysis).[1]

Scheme 1: CPA derivatives available from Solvias. The derivatives in gray will be available in fall 2017.

The nature of the phosphoric acid, being a Brønsted acid and a Lewis base, allows for different activation modes (mono-, dual-, bifunctional activation) resulting in a plethora of possible catalytic transformations. The 3,3’-substitution pattern provides a narrow, well-defined and tunable cavity which in combination with the axially chiral backbone is responsible for the induction of high chemo- as well as enantioselectivities.

Scheme 2: Selection of CPA-catalyzed reactions reported in literature.[2]

Our new synthetic approach not only enables us to provide these new products in high-quality but also in multi-kg amounts. The binaphthol based chiral phosphoric acids are available in the following package sizes:

  Price Price/g
1g 500 CHF 500 CHF/g
5g 2'250 CHF 450 CHF/g
10g 4'250 CHF 425 CHF/g
25g 9'750 CHF 390 CHF/g
50g 17'500 CHF 350 CHF/g
BULK upon request  

Our portfolio of CPA will be further expanded in the coming months. We cordially invite you to suggest additional derivatives!

[1] D. Parmar, E. Sugino, S. Raja, M. Rueping, Chem. Rev. 2014, 114, 9047.

[2] (a) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem., Int. Ed. 2004, 43, 1566. (b) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356. (c) W. Kashikura, K. Mori, T. Akiyama, Org. Lett. 2011, 13, 1860. (d) T. Akiyama, T. Katoh, K. Mori, Angew. Chem., Int. Ed. 2009, 48, 4226. (e) Jain, P.; Antilla, J. C. J. Am. Chem. Soc. 2010, 132, 11884. (f) Rueping, M.; Sugiono, E.; Azap, C.; Thiessman, T.; Bolte. M. Org. Lett. 2005, 7, 3781. (g) Hoffmann, S.; Seayad, A.; List, B. Angew. Chem. Int. Ed. 2005, 44, 7424. (h) Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W.C. J. Am. Chem. Soc. 2006, 128, 84.

 

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