Stereoselective Synthesis of -Amino Ketones: A Three-Component Mannich-Type Reaction of Aromatic Aldehydes, Anilines, and Cyclohexanone Using Amberlyst-15

Synthetic Communications

Volumn 39, Issue 17, 2009, Pages 3111-3118

  Das, Biswanath ^a   Kumar, Avula Satya ^a   Kanth, Bommena Ravi ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

amino ketone; Amberlyst 15; Mannich type reaction; Stereoselective synthesis; Three component reaction

Indexed keywords

2 [(4 BROMOPHENYLAMINO)(4 CHLOROPHENYL)METHYL]CYCLOHEXANONE; 2 [(4 BROMOPHENYLAMINO)(PHENYL)METHYL]CYCLOHEXANONE; 2 [(4 CHLOROOPHENYL)(PHENYLAMINO)METHYL]CYCLOHEXANONE; ALDEHYDE; ANILINE DERIVATIVE; BETA AMINO KETONE DERIVATIVE; CYCLOHEXANONE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; MANNICH REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 68749099622     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902730960     Document Type: Article

References (17)

1. Arend, M.; Westerman, B.; Risch, N. Modern variants of the Mannich reaction. Angew. Chem. Int. Ed. 1988, 37, 1044.
2. Rosenblum, S. B.; Huynth, T.; Afonso, A.; Davis, H. R. Jr.; Yumibe, N.; Clader, J. W.; Burnet, D. A. Discovery of 1-(4-fluorophenyl)-(3R)-[3-(4- fluorophenyl)-(3S)-hydroxypropyl]-(4S)-(4-hydroxyphenyl) -2-azetidinone (SCH 58235): A designed, potent, orally active inhibitor of cholesterol absorption. J. Med. Chem. 1998, 41, 973.
3. Cheng, R. P.; Gellman, S. H.; De Grado, W. F. β-Peptides from structure to function. Chem. Rev. 2001, 101, 3219.
4. Nicolaou, K. C.; Dai, W. M.; Guy, R. K. Chemistry and biology of taxol. Angew. Chem. Int. Ed. 1994, 33, 15.
5. Davis, F. A.; Szewezyk, J. M. Synthesis and applications of nonracemic β-amino aldehydes to the asymmetric synthesis of piperdines: (+)-Dihydropinidine. Tetrahedron Lett. 1988, 39, 5951.
6. List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. The proline-catalyzed direct asymmetric three-component Mannich reaction: Scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols. J. Am. Chem. Soc. 2002, 124, 827.
7. Trost, B. M.; Terrell, L. R. A direct catalytic asymmetric Mannich-type reaction to syn-amino alcohols. J. Am. Chem. Soc. 2003, 125, 338.
8. Ibrahem, I.; Zou, W. B.; Enggvist, M.; Xu, Y. M.; Cordova, A. Acyclic chiral amines and amino acids as inexpensive and readily tunable catalysts for the direct asymmetric three-component Mannich reaction. Chem - Eur. J. 2005, 11, 7024.
9. 2-catalyzed Mannich-type reaction. Tetrahedron Lett. 2006, 47, 1845.
10. Azizi, N.; Torkiyon, L.; Saidi, M. R. Highly efficient one-pot three-component Mannich reaction in water catalyzed by heteropoly acids. Org. Lett. 2006, 8, 2079.
11. 2-catalyzed stereoselective synthesis of β-amino ketones via a direct Mannich-type reaction. Tetrahedron Lett. 2007, 8, 6801.
12. Das, B.; Ramu, R.; Ravikanth, B.; Reddy, K. R. Regioselective ring opening of aziridines with potassium thiocyanate and thiols using sulfated zirconia as a heterogeneous recyclable catalyst. Tetrahedron Lett. 2006, 47, 779.
13. Das, B.; Venkateswarlu, K.; Holla, H.; Krishnaiah, M. Sulfonic acid functionalized silica: A remarkable efficient heterogeneous reusable catalyst for α-monobromination of carbonyl compounds using N-bromosuccinimide. J. Mol. Catal. A: Chem. 2006, 253, 107.
14. 2). Helv. Chem. Acta 2007, 90, 340.
15. 2 as a heterogeneous recyclable catalyst. Tetrahedron Lett. 2007, 48, 5371.
16. Loh, T. P.; Liung, S. B. K. W.; Tan, K. L.; Wei, L. L. Three component synthesis of β-amino carbonyl compounds using indium trichloride-catalyzed one-pot Mannich-type reaction in water. Tetrahedron 2000, 56, 3227.
17. Ollevier, T.; Nadeau, E. Bismuth triflate-catalyzed three-component Mannich-type reaction. J. Org. Chem. 2004, 69, 9292.