A Practical synthesis of 3-Acyl cyclobutanones by [2 〈 2] annulation. Mechanism and utility of the zn(II)-Catalyzed condensation of r-Chloroenamines with electron-deficient alkenes

Journal of Organic Chemistry

Volumn 76, Issue 6, 2011, Pages 1662-1672

  O'Brien, Jeannette M ^a   Kingsbury, Jason S ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AB INITIO CALCULATIONS; AMBIENT TEMPERATURES; CYCLOADDITION REACTION; CYCLOBUTANONES; DUAL ROLE; ELECTRON-DEFICIENT; QUATERNARY CARBON; TERTIARY AMIDES; UNSATURATED CARBONYL COMPOUNDS;

AMIDES; CALCULATIONS; CARBONYLATION; CYCLOADDITION; KETONES; OLEFINS; UNSATURATED COMPOUNDS; ZINC; ZINC COMPOUNDS;

CATALYSIS;

1 CHLORO 1 CYCLOHEPTYLIDENE N,N DIMETHYLMETHANAMINE; 1 CHLORO 1 CYCLOHEXYLIDENE N,N DIMETHYLMETHANAMINE; 2,2 DIMETHYL 3 (1 OCTENYL)CYCLOBUTANONE; 2,2 DIMETHYL 3 (PARA METHOXYPHENYL)CYCLOBUTANONE; 2,2 DIMETHYL 3 (PARA NITROPHENYL)CYCLOBUTANONE; 2,2 DIMETHYL 3 OXOCYCLOBUTANECARBOXYLIC ACID; 2,2 DIMETHYL 3 PHENYLCYCLOBUTANONE; 3 ACETYL 2,2 DIMETHYLCYCLOBUTANONE; 3 ACETYL 2,2,3 TRIMETHYLCYCLOBUTANONE; ALKENE; AMIDE; CARBON; CARBONYL DERIVATIVE; CYCLOBUTANONE DERIVATIVE; ENAMINE; IMINE; KETENIMINIUM; METHYL 1,2,2 TRIMETHYL 3 OXOCYCLOBUTANECARBOXYLATE; METHYL 2,2 DIMETHYL 3 OXOCYCLOBUTANECARBOXYLATE; METHYL 3 OXOSPIRO[3.6]DECANE 1 CARBOXYLATE; N METHOXY N METHYLMETHACRYLAMIDE; N METHOXY N,1,2,2 TETRAMETHYL 3 OXOCYCLOBUTANECARBOXAMIDE; N METHOXY N,2,2 TRIMETHYL 3 OXOCYCLOBUTANECARBOXAMIDE; N,N DIMETHYLCYCLOHEPTANECARBOXAMIDE; N,N,1,2,2 PENTAMETHYL 3 OXOCYCLOBUTANECARBOXAMIDE; N,N,2,2 TETRAMETHYL 3 OXOCYCLOBUTANECARBOXAMIDE; SOLVENT; UNCLASSIFIED DRUG; ZINC ION;

AB INITIO CALCULATION; ANNULATION REACTION; ARTICLE; ATOM; CATALYSIS; CYCLOADDITION; DRUG SYNTHESIS; ELECTRON; ENVIRONMENTAL TEMPERATURE; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

ALKENES; BIPHENYL COMPOUNDS; BUTANONES; CATALYSIS; ELECTRON TRANSPORT; ELECTRONS; IMIDAZOLES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; QUANTUM THEORY; ZINC;

EID: 79953873667     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102257k     Document Type: Article

References (54)

1. (a) Ischay, M. A.; Lu, Z.; Yoon, T. P. J. Am. Chem. Soc. 2010, 132, 8572-8574.
2. (b) For details on a stereocontrolled approach to tetrasubstituted cyclobutanes and its applications in synthesis, see: (b) Baran, P. S.; Li, K.; O'Malley, D. P.; Mitsos, C. Angew. Chem., Int. Ed. 2006, 45, 249-252.
3. (c) O'Malley, D. P.; Li, K.; Maue, M. A.; Zografos, L.; Baran, P. S. J. Am. Chem. Soc. 2007, 129, 4762- 4775.
4. (d) For Brønsted or Lewis acid-catalyzed [2 〈 2] cyclizations based on tandem Michael- Aldol sequences, see: (d) Inanaga, K.; Takasu, K.; Ihara, M. J. Am. Chem. Soc. 2005, 127, 3668-3669.
5. (e) Boxer, M. B.; Yamamoto, H. Org. Lett. 2005, 7, 3127- 3129.
6. (a) Reviews on [2 〈 2] photocycloaddition: (a) Crimmins, M. T.; Reinhold, T. L. Org. React. 1993, 44, 297-588.
7. (b) Bach, T. Synthesis 1998, 683- 703.
8. (c) Hoffman, N. Chem. Rev. 2008, 108, 1052- 1103.
9. (d) Select recent studies: (d) Mangion, I. K.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3696-3697.
10. (e) Ng, S. M.; Bader, S. J.; Snapper, M. L. J. Am. Chem. Soc. 2006, 128, 7315- 7319.
11. (f) Shen, R.; Corey, E. J. Org. Lett. 2007, 9, 1057- 1059.
12. (a) Marrero, J.; Rodríguez, A. D.; Baran, P.; Raptis, R. G. Org. Lett. 2003, 5, 2551-2554.
13. For synthetic studies toward providencin, see: (b) Bray, C. D.; Pattenden, G. Tetrahedron Lett. 2006, 47, 3937-3939.
14. (c) Schweizer, E.; Gaich, T.; Brecker, L.; Mulzer, J. Synthesis 2007, 3807- 3814.
15. (d) Gaich, T.; Arion, V.; Mulzer, J. Heterocycles 2007, 74, 885- 862.
16. (e) White, J. D.; Jana, S. Org. Lett. 2009, 11, 1433- 1436.
17. A recent review on the chemistry of furanocembranes and pseudopteranes: (f) Roethle, P. A.; Trauner, D. Nat. Prod. Rep. 2008, 25, 298- 317.
18. Nozaki, H.; Hayashi, K.-I.; Kido, M.; Kakumoto, K.; Ikeda, S.; Matsuura, N.; Tani, H.; Takaoka, D.; Iinuma, M.; Akao, Y. Tetrahedron Lett. 2007, 48, 8290-8292. C8/C80 relative configuration is still unknown.
19. Recent total syntheses of other cyclobutane-containing targets: (a) Tsai, A. S.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 6316-6317.
20. (b) Nicolaou, K. C.; Wu, T. R.; Sarlah, D.; Shaw, D. M.; Rowcliffe, E.; Burton, D. R. J. Am. Chem. Soc. 2008, 130, 11114- 11121.
21. Other catalytic entries to [2 〈 2] cycloaddition rely on ynamide functionality; see: (a) Li, H.; Hsung, R. P.; DeKorver, K. A.; Wei, Y. Org. Lett. 2010, 12, 3780-3783.
22. Couty, S.; Meyer, C.; Cossy, J. Angew Chem., Int. Ed. 2006, 45, 6726-6730 and references therein.
23. (a) Marchand-Brynaert, J.; Ghosez, L. J. Am. Chem. Soc. 1972, 94, 2870-2872.
24. (b) De Poortere, M.; Marchand-Brynaert, J.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1974, 13, 267.
25. (c) Falmagne, J.-B.; Escudero, J.; Taleb-Sahraoui, S.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1981, 20, 879-880.
26. (d) Houge, C.; Frisque-Hesbain, A. M.; Mockel, A.; Ghosez, L. J. Am. Chem. Soc. 1982, 104, 2920- 2921.
27. (e) Saimoto, H.; Houge, C.; Hesbain-Frisque, A. M.; Mockel, A.; Ghosez, L. Tetrahedron Lett. 1983, 24, 2251-2254.
28. (f) Markó, I.; Ronsmans, B.; Hesbain-Frisque, A. M.; Dumas, S.; Ghosez, L. J. Am. Chem. Soc. 1985, 107, 2192- 2194.
29. See also: (g) Chen, L.-Y.; Ghosez, L. Tetrahedron Lett. 1990, 31, 4467- 4470.
30. For a review, see: (a) Snider, B. B. Chem. Rev. 1988, 88, 793-811.
31. For an application in total synthesis relying on unconventional conditions for ketene formation, see: (b) Mushti, C. S.; Kim, J.-H.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 14050-14052.
32. (a) Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Academic Press: New York, 1969.
33. (b) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: Chichester, U.K., 1976; pp 143-147.
34. Corey, E. J.; Desai, M. C. Tetrahedron Lett. 1985, 26, 3535-3538.
35. Heine, H.-G.; Hartmann, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 782-783.
36. Devos, A.; Remion, J.; Frisque-Hesbain, A.-M.; Colens, A.; Ghosez, L. Chem. Commun. 1979, 1180-1181.
37. Bendall, J. G.; Payne, A. N.; Screen, T. E. O.; Holmes, A. B. Chem. Commun. 1997, 1067-1068.
38. Weingarten, H. J. Org. Chem. 1970, 35, 3970-3971.
39. Other Lewis acids screened include AlCl3, TiCl4, SnCl4, and Sc(OTf) 3.
40. For other representative examples of [2 〈 2] cycloaddition reactions that benefit from ultrasonic activation, see: (a) Ref 7g.
41. (b) Chen, X.-T.; Bhattacharya, S. K.; Zhou, B.; Gutteridge, C. E.; Pettus, T. R. R.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 6563- 6579.
42. A competing oligomerization of the acrylic ester may account for the diminished yield in these cases since a highly polar yet intractable fraction is visible as a baseline spot in the TLC of the crude reaction mixtures.
43. (a) Haveaux, B.; Dekoker, A.; Rens, M.; Sidani, A. R.; Toye, J.; Ghosez, L. Organic Syntheses; Wiley & Sons: New York, 1988; Collect. Vol. No. 6, pp 282-286.
44. (b) Ghosez, L.; George-Koch, I.; Patiny, L.; Houtekie, M.; Bovy, P.; Nshimyumukiza, P.; Phan, T. Tetrahedron 1998, 54, 9207- 9222.
45. Our attempt to use a stereoisomeric mixture of the β-benzyl, N, N-dimethyl α-chloroenamine without isolation was not successful, presumably due to competing oligomerization of this reactant at the warmer temperatures required for cyclocondensation. In addition, N,Ndiethyl- 2-phenylpropanamide failed to chlorinate efficiently under standard conditions with oxalyl chloride, presumably due to steric hindrance.
46. Checkers of the Organic Syntheses prep (ref 18a) also observed that early fractions of 7 boiling at 100-125 °C were mixtures of product and triethylamine.
47. Chen, B.-C.; Ngu, K.; Guo, P.; Liu, W.; Sundeen, J. E.; Weinstein, D. S.; Atwal, K. S.; Ahmad, S. Tetrahedron Lett. 2001, 42, 6227-6229.
48. The intermediates play a role in other reactions that begin with protonation or alkylation of nucleophilic ynamides. See: (a) Zhang, Y.; Hsung, R. P.; Zhang, X.; Huang, J.; Slafer, B. W.; Davis, A. Org. Lett. 2005, 7, 1047-1050 for a specific example.
49. See: (b) DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Shi, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064-5106 for a recent review.
50. For another unexpected regiochemical outcome in a ketene cycloaddition reaction involving an electron-rich double bond, see: Cagnon, J. R.; Bideau, F. L.; Marchand-Brynaert; Ghosez, L. Tetrahedron Lett. 1997, 38, 2291-2294.
51. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.
52. Maegawa, T.; Akashi, A.; Sajiki, H. Synlett 2006, 1440-1442.
53. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818.
54. Sengmany, S.; Léonel, E.; Paugam, J. P.; Nédélec, J.-Y. Tetrahedron 2002, 58, 271-277.