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Proline Based Organocatalysts

Prolinamide organocatalyst plays increasing role in asymmetric synthesis

During the last two decades proline and pyrrolidine organocatalysts have emerged as an efficient and cost-effective alternative to catalysis with expensive precious metals. They also have exceptional chemical properties that result in high enantioselectivities. The basic l-Proline is a bifunctional molecule with both carboxylic acid and amine groups in the same molecule. These two functional groups are able to act as acid or base and can facilitate chemical transformations conceptually similar to enzymatic catalysis [1].

Image1

Proline is one of the most successful and widely studied secondary amine-based organocatalysts. It can catalyze numerous reactions such as aldol, Mannich, and Michael additions, the Robinson annulation, Diels-Alder, α-functionalization, α-amination and α-aminoxylation reactions. Catalytic and enantioselective α-oxygenation of carbonyl compounds are important reactions to access a variety of useful building blocks for bioactive molecules [2-10].

Currently, Strem in collaboration with Daicel, offers the following Proline and Pyrrolidin based asymmetric organocatalysts:

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Image3  Image4  Image5

 

Chiral amino alcohols such as 07-1170, 07-1171 and 07-7234 are used in asymmetric Michael reactions [11], aldol condensations [12], asymmetric transfer reactions [13], as well as for synthesis of complex organic, bioorganic molecules and natural products [e.g. 14]. l-Prolinamide organocatalysts 07-0983 and 07-0984 facilitate aldol reactions [15], enantioselective conjugate additions [16], and organocatalytic asymmetric Mannich [17] and Michael reactions [18].

 

References:

  1. Tetrahedron 2002, 58, 5573.
  2. Adv. Synth. Catal., 2009, 351, 33.
  3. Chem. Soc. Rev., 2010, 39, 1600.
  4. Acc. Chem. Res., 2013, 46, 289.
  5. Chem. Eur. J., 2013, 19, 3573.
  6. Chem. Rev. 2014, 114, 2130.
  7. ACS Catal. 2015, 5, 1972.
  8. Org. Biomol. Chem., 2016, 14, 6147.
  9. Acc. Chem. Res., 2017, 50, 2936.
  10. Catal. Sci. Technol., 2018, 8, 389.
  11. Eur. J. Org. Chem., 2018, (48), 6843.
  12. Org. Lett., 2018, 20, 1232.
  13. Tetrahedron Asymmetry 2005, 16, 2299.
  14. Chem. Eur. J., 2018, 24, 16543.
  15. Chem. Commun., 2006, (4), 429.
  16. Eur. J. Org. Chem., 2007, (14), 2328.
  17. Can. J. Chem., 2016, 94, 769.
  18. Org. Biomol. Chem., 2013, 11, 443.

 

Products mentioned in this blog:

07-1170: Nitrogen › (2R)-(-)-N-Methyl-α,α-diphenyl-2-pyrrolidinemethanol, min. 98% (144119-12-0)
07-1171: Nitrogen › (2S)-(+)-N-Methyl-α,α-diphenyl-2-pyrrolidinemethanol, min. 98% (110529-22-1)
07-7234: Nitrogen › (R)-Diphenylprolinol trimethyl silyl ether, 95% (99% ee) (943757-71-9)
07-0983: Nitrogen › (2S)-N-[(1S,2R)-2-Hydroxy-1,2-diphenylethyl]-2-pyrrolidinecarboxamide, 98%, (99% ee) (529486-25-7)
07-0984: Nitrogen › (2S)-N-[(1R,2S)-2-Hydroxy-1,2-diphenylethyl]-2-pyrrolidinecarboxamide, 98%, (99% ee) (529486-23-5)
07-5610: Nitrogen › 3-[[3,5-Bis(trifluoromethyl)phenyl]amino]-4-[[(1R,2R)-2-(1-piperidinyl)cyclohexyl]amino]-3-cyclobutene-1,2-dione, 98% (1211565-11-5)
07-1350: Nitrogen › 1-[3,5-Bis(trifluoromethyl)phenyl]-3-[(1R,2R)-2-(pyrrolidin-1-yl)cyclohexyl]thiourea, 98%, (99% ee) (1314743-49-1)
07-0912: Nitrogen › N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(2S)-2-pyrrolidinylmethyl]thiourea, 98% (904928-30-9)

Related Materials:
High Purity Chiral Reagents sold in collaboration with Daicel
Catalysts & Chiral Catalysts
Organocatalyst
Metal Catalysts for Organic Synthesis
Chiral Phosphoric Acids

 

 

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