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SPINOL Chiral Phosphoric Acids (PA)

Broad array of SPINOL phosphoric acid catalysts introduced for asymmetric synthesis

In one of our blogs, we reviewed a large collection of BINOL chiral phosphoric acids and only one SPINOL-derived phosphoric acid (15-0542). Since then, our product line of SPINOL organocatalysts has substantially expanded with now up to 20 products. BINOL-phosphate related catalytic processes have been intensively studied during the last couple of decades. However, the application of SPIROL-derived phosphoric acids is relatively new and less studied, therefore, research in this unexplored field is more prospective. The list of our new SPINOL products is summarized in table 1. 

Table 1. List of new SPINOL phosphoric acids

Image1

R = 2,4,6-tri-isopropylphenyl 15-0574                                   S = 2,4,6-tri-isopropylphenyl 15-0564

            R = 4-(trifluoromethyl)phenyl 15-0484                    S = 4-(trifluoromethyl)phenyl 15-0492

                   R = 4-methoxyphenyl 15-0494                                          S = 4-methoxyphenyl 15-0508

                       R = 4-nitrophenyl 15-0576                                                 S = 4-nitrophenyl 15-0512

                  R = 3,5-dichlorophenyl 15-0514                                       S = 3,5-dichlorophenyl 15-0516

                        R = triphenylsilyl 15-0520                                                   S = triphenylsilyl 15-0524

                 R = 3,5-diphenyl-phenyl 15-0526                                   S = 3,5-diphenyl-phenyl 15-0530

  R = 3,5-bis(tert-butyl)-4-methoxyphenyl 15-0532        S = 3,5-bis(tert-butyl)-4-methoxyphenyl 15-0534

               R = 2,4,6-trimethylphenyl 15-0538                               S = 2,4,6-trimethylphenyl 15-0544

            R = 4-(2-naphthalenyl)phenyl 15-0546                    S = 4-(2-naphthalenyl)phenyl 15-0548

 

The chemical behavior and structural peculiarities of BINOL and SPINOL chiral phosphoric acids is well reviewed in the literature [1-3] as well as in our blog; Chiral Phosphoric Acid Catalysts for Asymmetric Synthesis.

There are many examples of the SPIROL-phosphate catalyzed reactions. In the asymmetric amination reaction SPIROL PA is acting together with Rh catalyst [4]. The asymmetric arylation of diazo compounds with aniline derivatives is co-catalyzed by an achiral dirhodium complex [5]. SPIROL PA acts as a pure organocatalyst in Friedel-Crafts reactions [6]; catalytic asymmetric Fischer indolization [7-8]; asymmetric protonation of silyl ketene imines[9]; enantioselective N–H insertion reactions [10] and others[11].

References:

  1.    Chem. Rev., 2014, 114, 9047.
  2.    Chem. Rev., 2015, 115, 9277.
  3.    Coord. Chem. Rev., 2016, 308, 131.
  4.    Chem. Commun., 2014, 50, 14639.
  5.    J. Am. Chem. Soc., 2015, 137, 8700.
  6.    J. Org. Chem., 2010, 75, 8677.
  7.    Angew. Chem. Int. Ed., 2013, 52, 9486.
  8.    Angew. Chem. Int. Ed., 2014, 53, 5202.
  9.    J. Am. Chem. Soc., 2013, 135, 2100.
  10.    Angew. Chem. Int. Ed., 2014, 53, 3913.
  11.    J. Am. Chem. Soc., 2016, 138, 16561.

 

Related Products & Resources:

Chiral Phosphoric Acids (Product Line)
Chiral Phosphoric Acids Literature Sheet
Chiral Phosphoric Acids Booklet
Ligands & Chiral Ligands
Metal Catalysts for Organic Synthesis Booklet
Phosphine
High Purity Chiral Reagents
Organocatalysts

 

 

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