Aziridines and aziridinium ions in the practical synthesis of pharmaceutical intermediates - A perspective

Current Opinion in Drug Discovery and Development

Volumn 5, Issue 6, 2002, Pages 918-927

  Dahanukar, Vilas H ^a   Zavialov, Ilia A ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Aziridination; Aziridines; Aziridinium ions; Nucleophilic ring opening reactions; Pharmaceutical intermediates; Process chemistry

Indexed keywords

1 (BENZOFURAN 2 YL) 2 PROPYLAMINOPENTANE; 5 BROMO N (1 ETHYL 4 METHYLHEXAHYDRO 1,4 DIAZEPIN 6 YL) 2 METHOXY 6 METHYLAMINONICOTINAMIDE; ALKENE; AMINOALCOHOL; ANTINEOPLASTIC AGENT; AZIRIDINE; BETASTATIN; CARBENE; CARBOXYLIC ACID; CHLORAMPHENICOL; DOPAMINE RECEPTOR BLOCKING AGENT; ECOPIPAM; ENZYME INHIBITOR; FURAN DERIVATIVE; IMINE; R 116010; SULFIDE; TOSYLCHLORAMIDE SODIUM; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; DRUG INDUSTRY; REVIEW; RING OPENING; STEREOCHEMISTRY; SYNTHESIS; TECHNIQUE;

ANIMALS; AZIRIDINES; HUMANS; IONS; PHARMACEUTICAL PREPARATIONS; TECHNOLOGY, PHARMACEUTICAL;

EID: 0036869010     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (38)

1. Pearson WH, Lian BW, Bergmeier SC: Monocyclic aziridines and azirines. In: Comprehensive Heterocyclic Chemistry, 2nd Edition. Padwa A (Ed), Elsevier Scientific, Oxford, UK (1996) 2:1-60. An extensive review on structure, synthesis, reactivity and applications of aziridines and azirines.
2. Zwanenburg B, ten Holte P: The synthetic potential of three-membered ring aza-heterocycles. Top Curr Chem (2001) 216:93-124. A recent update on aziridine chemistry and utility of aziridine esters in the synthesis of amino acids and heterocycles.
3. McCoull W, Davis FA: Recent synthetic applications of chiral aziridines. Synthesis (2000) 10:1347-1365.
4. Osborn HMI, Sweeney J: The asymmetric synthesis of aziridines. Tetrahedron Asymmetry (1997) 8:1693-1715.
5. Gillespie KM, Sanders CJ, O'Shaughnessy P, Westmoreland I, Thickitt CP, Scott P: Enantioselective aziridination using copper complexes of biaryl schiff bases. J Org Chem (2002) 67:3450-3458.
6. Dauban P, Sainère L, Tarrade A, Dodd RH: Copper-catalyzed nitrogen transfer mediated by iodosylbenzene Phl=O. J Am Chem Soc (2001) 123:7707-7708.
7. Loncaric C, Wulff WD: An efficient synthesis of (-)-chloramphenicol via asymmetric catalytic aziridination: A comparison of catalysts prepared from triphenylborate and various linear and vaulted biaryls. Org Lett (2001) 3:3675-3678.
8. Aggarwal VK, Alonso E, Fang G, Ferrara M, Hynd G, Porcelloni M: Application of chiral sulfides to catalytic asymmetric aziridination and cyclopropanation with in situ generation of the diazo compound. Angew Chem Int Ed (2001) 40:1433-1436. A novel method for catalytic asymmetric aziridination of olefins, in which carbenes are generated in situ from tosylhydrazone salts.
9. Bergmeier SC: The synthesis of vicinal amino alcohols. Tetrahedron (2000) 56:2561-2576.
10. CRC Handbook of Optical Resolutions via Diastereomeric Salt Formation. Kozma D (Ed), CRC Press, Boca Raton, FL, USA (2002).
11. Chuang TH, Sharpless KB: Applications of aziridinium ions. Selective syntheses of β-aryl-α,β-diamino esters. Org Lett (1999) 1:1435-1437. Chloramines are isolated, characterized and utilized as latent forms of aziridinium ions.
12. Andrews DR, Dahanukar VH, Eckert JM, Gala D, Lucas BS, Schumacher DP, Zavialov IA: Reaction of aziridinium ions with organometallic reagents: Optimization of the key step of ecopipam synthesis. Tetrahedron Lett (2002) 43:6121-6125. A report on the formation of aziridinium ions and their reaction with aryl Grignard reagents.
13. Jeong JU, Tao B, Sagasser I, Henniges H, Sharpless KB. Bromine-catalyzed aziridination of olefins. A rare example of atom-transfer redox catalysis by a main group element J Am Chem Soc (1998) 120:6844-6845. A general practical method for synthesis of N-tosyl aziridines from olefins.
14. Caine D, O'Brien P, Rosser CM: Diastereocontrolled synthesis of trans-and cis-meso-cyclopentene aziridines. Org Lett (2002) 4:1923-1926.
15. 2 system under phase transfer catalysis conditions. J Chem Soc Perk Trans 1 (2001) 23:3186-3188.
16. Siu T, Yudin AK: Practical olefin aziridination with a broad substrate scope. J Am Chem Soc (2002) 124:530-531.
17. Farthing CN, Baldwin JE, Russel AT, Schofield CJ, Spivey AC: Syntheses of (S)-β-pyrazolylalanine and (S)-quisqualic acid from a serine-derived aziridine. Tetrahedron Lett (1996) 37:5225-5226.
18. O'Brien P, Towers TD: Diamine synthesis: Exploring the regioselectivity of ring opening of aziridinium ions. J Org Chem (2002) 67:304-307.
19. Katagiri T, Takahashi M, Fujiwara Y, Ihara H, Uneyama K: General syntheses of optically active α-trifluoromethylated amines via ring opening reactions of N-benzyl-2-trifluoromethylaziridine. J Org Chem (1999) 64:7323-7329.
20. Acar EA, Glamer F, Burger U: Aminocyclopentitols from N-alkylpyridinium salts: A photochemical approach. Helv Chim Acta (1998) 81:1095-1104.
21. N2′ ring opening of aziridines bearing an α,β-unsaturated ester group with organocopper reagents. A new stereoselective synthetic route to (E)-alkene dipeptide isosteres. J Chem Soc Perk Trans 1 (1995) 76:1359-1371.
22. Stamm H, Speth D: Reactions with aziridines. XLVII. Regiospecificity and stereoselectivity of acid-catalyzed alcoholysis of cis-2-benzyl-3-phenyl-1-(phenylsulfonyl)-aziridine. Arch Pharm (1989) 322:277-279.
23. Wade TN: Preparation of fluoro amines by the reaction of aziridines with hydrogen fluoride in pyridine solution. J Org Chem (1980) 45:5328-5333.
24. Weber K, Kuklinski S, Gmeiner P: Treatment of N,N-dibenzylamino alcohols with sulfonyl chloride leads to rearranged β-chloro amines, precursors to β-amino acids, and not tetrahydrosioquinolines. Org Lett (2000) 2:647-649.
25. Dieter RK, Deo N, Lagu B, Dieter JW: Stereo- and regioselective synthesis of chiral diamines and triamines from pseudoephedrine and ephedrine. J Org Chem (1992) 57:1663-1671.
26. Davis FA, Reddy GV, Liang CH: Aziridine 2-carboxylate ester mediated asymmetric synthesis of α-alkyl β-amino acids. Tetrahedron Lett (1997) 38:5139-5142.
27. Falkenstein R, Mall T, Speth D, Stamm H: Single electron transfer versus nucleophilic ring opening in reactions of cistrans pairs of activated 2-phenylaziridines. Strong influence of nitrogen pyramid for N-benzoylaziridines. J Org Chem (1993) 58:7377-7381.
28. Stamm H: Nucleophilic ring opening of aziridines. J Prakt Chem (1999) 341:319-331.
29. Maligres PE, See MM, Askin D, Reider PJ: Nosylazirdines: Activated aziridine electrophile. Tetrahedron Lett (1997) 38:5253-5256.
30. Gontcharov AV, Liu H, Sharpless KB: tert-Butylsulfonamide. A new nitrogen source for catalytic aminohydroxylation and aziridination of olefins. Org Lett (1999) 1:783-786.
31. Hu XE, Kim NK, Ledoussal B, Colson AO: Regio- and stereocontrolled copper organometallic addition to a piperidinyl aziridine: Synthesis of trans 3-amino-4-alkyl-piperidines. Tetrahedron Lett (2002) 43:4289-4293.
32. Hirokawa Y, Horikawa T, Noguchi H, Yamamoto K, Kato S: Process development of the synthetic route to (R-)-6-amino-1-ethyl-4-methylhexahydro-1,4-diazepine. Org Process Res Dev (2002) 6:28-35.
33. Aelterman W, Lang Y, Willemsens B, Vervest I, Leurs S, De Knaep F: Conversion of the laboratory synthetic route of the N-aryl-2-benzothiazolamine R116010 to a manufacturing method. Org Process Res Dev (2001) 5:467-471.
34. Totleben MJ, Freeman JP, Szmuszkovicz J: Imidazole transfer from 1,1′-carbonyldiimidazole and 1,1′-(thiocarbonyl)diimidazole to alcohols. A new protocol for the conversion of alcohols to alkylheterocycles. J Org Chem (1997) 62:7319-7323.
35. Hou D, Schumacher D: The selection of a commercial route for the D, antagonist Sch-39166. Curr Opin Drug Discovery Dev (2001) 4:792-799.
36. Liu Q, Marchington AP, Rayner CM: Synthesis of new potential aminopeptidase inhibitors by Lewis acid induced rearrangement of 2,3-epoxy amines and regiospecific nucleophilic trapping of aziridinium ion intermediates with α-amino esters. Tetrahedron (1997) 53:15729-15742.
37. CHEMBIONEX CO LTD (Won L, Park C, Yeon L): Optically active aziridine-2-carboxylate derivatives and a process for preparing them. WO-00212186 (2002).
38. FUJIMOTO PHARMACEUTICAL CO (Yoneda F, Watanabe M, Oka T, Yasusa T): Process for preparing optically active aminopentane derivatives. WO-00177074 (2001).