Chiral ammonium betaines: A bifunctional organic base catalyst for asymmetric mannich-type reaction of α-nitrocarboxylates

Journal of the American Chemical Society

Volumn 130, Issue 33, 2008, Pages 10878-10879

  Uraguchi, Daisuke ^a   Koshimoto, Kyohei ^a   Ooi, Takashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM DERIVATIVE; BETAINE; CARBOXYLIC ACID DERIVATIVE; IMINE; ORGANIC COMPOUND;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; MANNICH REACTION; STEREOCHEMISTRY;

EID: 50249092090     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8041004     Document Type: Article

References (14)

1. (a) Jones, R. A. Quaternary Ammonium Salts: Their use in Phase-Transfer Catalysis; Academic Press: London, U.K., 2001.
2. (b) Asymmetric Phase Transfer Catalysis; Maruoka, K., Ed.; Wiley-VCH: Weinheim, Germany, 2008.
3. Review of bifunctional metal catalysis: Shibasaki, M.; Matsunaga, S. Chem. Soc. Rev. 2006, 35, 269, and references therein.
4. Reviews of organocatalysis: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
5. (b) Pellissier, H. Tetrahedron 2007, 63, 9267.
6. For reviews on organocatalyzed Mannich-type reactions, see: (a) Ting, A.; Schaus, S. E. Eur. J. Org. Chem. 2007, 5797.
7. (b) Verkade, J. M. M.; van Hemert, L. J. C.; Quaedflieg, P. J. L. M.; Rutjes, F. P. J. T. Chem. Soc. Rev. 2008, 37, 29.
8. 2O, forming intramolecular ion-pairing 2. We also confirmed that 1 itself could not catalyze the present Mannich-type reaction at all.
9. (a) Knudsen, K. R.; Jørgensen, K. A. Org. Biomol. Chem. 2005, 3, 1362.
10. (b) Chen, Z.; Morimoto, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 2170.
11. (c) Singh, A.; Johnston, J. N. J. Am. Chem. Soc. 2008, 130, 5866.
12. 3 (see the Supporting Information).
13. was prepared from the corresponding ammonium hydroxide according to the literature procedure: Tozawa, T.; Nagao, H.; Yamane, Y.; Mukaiyama, T. Chem. Asian J. 2007, 2, 123.
14. For the catalysis of intermolecular ion-pairing, chiral quaternary ammonium phenoxide, see ref 8 and references therein.