Synthesis of chiral aziridines through decarboxylative generation of sulfur ylides and their reaction with chiral sulfinyl imines

Synthetic Communications

Volumn 39, Issue 13, 2009, Pages 2405-2422

  Forbes, David C ^a   Bettigeri, Sampada V ^a   Amin, Sejal R ^a   Bean, Christie J ^a   Law, Amanda M ^a   Stockman, Robert A ^b  

^a UNIVERSITY OF SOUTH ALABAMA   (United States)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Asymmetry; Aziridination; Methylene transfer; S ylide

Indexed keywords

1 [(1,1 DIMETHYLETHYL)SULFINYL] 2 (2,6 DICHLOROPHENYL)AZIRIDINE; 1 [(1,1 DIMETHYLETHYL)SULFINYL] 2 (3,4 METHYLENEDIOXYPHENYL)AZIRIDINE; 1 [(1,1 DIMETHYLETHYL)SULFINYL] 2 (4 CHLOROPHENYL)AZIRIDINE; 1 [(1,1 DIMETHYLETHYL)SULFINYL] 2 (4 HYDROXY 3 METHOXYPHENYL)AZIRIDINE; 1 [(1,1 DIMETHYLETHYL)SULFINYL] 2 (4 METHOXYPHENYL)AZIRIDINE; 1 [(1,1 DIMETHYLETHYL)SULFINYL] 2 (4 NITROPHENYL)AZIRIDINE; 1 [(1,1 DIMETHYLETHYL)SULFINYL] 2 PHENYLAZIRIDINE; 2 METHYL N [(2,6 DICHLOROPHENYL)METHYLENE] 2 PROPANESULFINAMIDE; 2 METHYL N [(3,4 METHYLENEDIOXYPHENYL)METHYLENE] 2 PROPANESULFINAMIDE; 2 METHYL N [(4 CHLOROPHENYL)METHYLENE] 2 PROPANESULFINAMIDE; 2 METHYL N [(4 HYDROXY 3 METHOXYPHENYL)METHYLENE] 2 PROPANESULFINAMIDE; 2 METHYL N [(4 METHOXYPHENYL)METHYLENE] 2 PROPANESULFINAMIDE; 2 METHYL N [(4 NITROPHENYL)METHYLENE] 2 PROPANESULFINAMIDE; 2 METHYL N [(PHENYL)METHYLENE] 2 PROPANESULFINAMIDE; AZIRIDINE DERIVATIVE; CARBENE; CARBOXYMETHYLSULFONIUM BETAINE; IMINE; SULFINYLIMINE DERIVATIVE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DECARBOXYLATION; DIASTEREOISOMER; ELECTRON TRANSPORT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 67650296949     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802654898     Document Type: Article

References (25)

1. (a) Yudin, A. (Ed.), Aziridines and Epoxides in Organic Synthesis; Wiley: New York, 2006;
2. (b) Trost, B. M.; Melvin, L. S. Jr. In Sulfur Ylides Emerging Synthetic Intermediates; Academic Press: New York, 1975; vol. 31;
3. (c)Nitrogen, Oxygen, and Sulfur Ylides Chemistry: A Practical Approach; J. S. Clark (Ed.); Oxford University Press: Oxford, 2002.
4. McGarrigle, E. M.; Myers, E. L.; Illa, O.; Shaw, M. A.; Riches, S. L.; Aggarwal, V. K. Chalcogenides as organocatalysts. Chem. Rev. 2007, 107, 5841.
5. (a) Dalko, P. I.; Moisan, L. In the golden age of organocatalysis. Angew. Chem., Int. Ed. 2004, 43, 5138;
6. (b) Dai, L.-X.; Hou, X.-L.; Zhou, Y.-G. Stereoselective synthesis of three-membered ring compounds via ylide routes. Pure Appl. Chem. 1999, 71, 369.
7. (a) Blot, V.; Brier, J.-F.; Davoust, M.; Miniere, S.; Reboul, V.; Metzner, P. Developments of asymmetric synthesis mediated by chiral sulfur reagents. Phosphorus, Sulfur, Silicon Relat. Elem. 2005, 180, 1171;
8. (b) Aggarwal, V. K. In Comprehensive Asymmetric Catalysis; E. N. Jacobsen, A. Pfaltz, H. Yamamoto, (Eds.); Springer-Verlag: Heidelberg, 1999; vol. 2, pp. 679-693;
9. (c) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Asymmetric ylide reactions: Epoxidation, cyclopropanation, aziridination, olefination, and rearrangement. Chem. Rev. 1997, 97, 2341;
10. (d) Stockman, R. A. Heterocyclic chemistry. Ann. Rep. Prog. Chem., Sec. B. 2004, 100, 149.
11. (a) Forbes, D. C.; Standen, M. C.; Lewis, D. L. Sulfur ylides via decarboxylation of carboxymethylsulfonium betaines: A novel and mild protocol for the preparation of oxiranes. Org. Lett. 2003, 5, 2283;
12. (b) Forbes, D. C.; Amin, S. R.; Bean, C. J.; Standen, M. C. Aryl-substituted sulfonium betaines: Preparation and use in the epoxidation of aldehydes. J. Org. Chem. 2006, 71, 8287.
13. (a) Cheng, J.-P.; Liu, B.; Zhang, X.-M. Radical substituent effects of a-sulfonium groups J. Org. Chem. 1998, 63, 7574;
14. (b) Johnson, A. W.; Amel, R. T. The chemistry of ylides, XVI: The acidifying effects of onium groups. Can. J. Chem. 1968, 46, 461.
15. (a) Chigboh, K.; Nadin, A.; Stockman, R. A. Direct synthesis of substituted vinyl aziridines. Synlett 2007, 18, 2879;
16. (b) Morton, D.; Stockman, R. A. Chiral non-racemic sulfinimines: Versatile reagents for asymmetric synthesis. Tetrahedron 2006, 62, 8869;
17. (c) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. A convenient synthesis of chiral nonracemic vinyl aziridines. Org. Lett. 2004, 6, 2377;
18. (d) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Corey-Chaykovsky reaction of chiral sulfinyl imines: A convenient procedure for the formation of chiral aziridines. Synlett 2003, 13, 1985.
19. Aggarwal, V. K.; Harvey, J. N.; Richardson, J. Unraveling the mechanism of epoxide formation from sulfur ylides and aldehydes. J. Am. Chem. Soc. 2002, 124, 5747.
20. Edwards, D. R.; Du, J.; Crudden, C. M. Experimental demonstration of base-catalyzed interconversion of isomeric betaine intermediates in the coreyćhaykovsky epoxidation. Org. Lett. 2007, 9, 2397.
21. Robiette, R. Mechanism and diastereoselectivity of aziridine formation from sulfur ylides and imines: A computational study. J. Org. Chem. 2006, 71, 2726.
22. 3 is-0.27 (-0.37 for OH). For a more extended list, see Ritchie, C. D.; Sager, W. F. An examination of structure-reactivity relationships Prog. Phys. Org. Chem. 1964, 2, 323, and Hansch, C.; Leo, A.; Unger, S.; Kim, K. H.; Nikaitani, D.; Liem, E. J. "Aromatic" substituent constants for structure-activity correlations. J. Med. Chem. 1973, 16, 1207.
23. Ardej-Jakuhisiak, M.; Kawecki, R.; Swietlinska, A. A facile synthesis of N-sulfinylaldimines. Tetrahedron: Asymmetry 2007, 18, 2507.
24. Morton, D. tert-Butyl-sulfinimines: A convinent synthesis of chiral aziridines (Ph.D thesis, University of East Anglia, Norwich, June 2005).
25. Plobeck, N.; Powell, D. Asymmetric synthesis of diarylmethylamines by diastereoselective addition of organometallic reagents to chiral N-tert-butanesulfinimines: Switchover of diastereofacial selectivity. Tetrahedron: Asymmetry 2002, 13, 303.