Catalytic asymmetric synthesis of 2,2-disubstituted oxetanes from ketones by using a one-pot sequential addition of sulfur ylide

Angewandte Chemie - International Edition

Volumn 48, Issue 9, 2009, Pages 1677-1680

  Sone, Toshihiko ^a   Lu, Gang ^a   Matsunaga, Shigeki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Asymmetric synthesis; Homogeneous catalysis; Oxetanes; Rare earth metals; Ylides

Indexed keywords

AMPLIFICATION; CATALYSIS; CHEMICAL COMPOUNDS; ELECTRON TRANSITIONS; KETONES; ORGANIC LIGHT EMITTING DIODES (OLED); RARE EARTH ELEMENTS; REACTION KINETICS; SULFUR; SYNTHESIS (CHEMICAL);

ASYMMETRIC SYNTHESIS; HOMOGENEOUS CATALYSIS; OXETANES; RARE-EARTH METALS; YLIDES;

COMPLEXATION;

ETHER DERIVATIVE; KETONE; LANTHANIDE; ORGANOPHOSPHORUS COMPOUND; OXETANE; SULFUR;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; ETHERS, CYCLIC; KETONES; METALS, RARE EARTH; ORGANOPHOSPHORUS COMPOUNDS; STEREOISOMERISM; SULFUR;

EID: 60749134502     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200805473     Document Type: Article

References (49)

1. Reviews and accounts on catalytic asymmetric epoxidations: a) E. N. Jacobsen, M. H. Wu in Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, p. 649;
2. b) T. Katsuki in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 287;
3. c) C. Bonini, G. Righi, Tetrahedron 2002, 58, 4981;
4. d) V. K. Aggarwal, C. L. Winn, Acc. Chem. Res. 2004, 37, 611;
5. e) Q.-H. Xia, H.-Q. Ge, C.-P. Ye, Z.-M. Liu, K.-X. Su, Chem. Rev. 2005, 105, 1603;
6. f) O. A. Wong, Y. Shi, Chem. Rev. 2008, 108, 3958.
7. Applications in medicinal chemistry: a) G. Wuitschik, M. Rogers-Evans, K. Müller, H. Fischer, B. Wagner, F. Schuler, L. Polonchuk, E. M. Carreira, Angew. Chem. 2006, 118, 7900;
8. Angew. Chem. Int. Ed. 2006, 45, 7736;
9. b) G. Wuitschik, M. Rogers-Evans, A. Buckl, M. Bernasconi, M. Märki, T. Godel, H. Fischer, B. Wagner, I. Parrilla, F. Schuler, J. Schneider, A. Alker, W. B. Schweizer, K. Müller, E. M. Carreira, Angew. Chem. 2008, 120, 4588;
10. Angew. Chem. Int. Ed. 2008, 47, 4512.
11. Selected recent examples in polymer and material science: a) Y. Permana, K. Nakano, M. Yamashita, D. Watanabe, K. Nozaki, Chem. Asian J. 2008, 3, 710;
12. b) H. Bouchekif, M. I. Philbin, E. Colclough, A. J. Amass, Macromolecules 2008, 41, 1989;
13. c) J. V. Crivello, J. Polym. Sci Part A 2007, 45, 4331.
14. a) M. M.-C. Lo, G. C. Fu, Tetrahedron 2001, 57, 2621, and references therein;
15. b) K. Soai, S. Niwa, T. Yamanoi, H. Hikima, M. Ishizaki, J. Chem. Soc. Chem. Commun. 1986, 1018;
16. c) F. Bertolini, S. Crotti, V. Di Bussolo, F. Macchia, M. Pineschi, J. Org. Chem. 2008, ASAP;
17. See also, d) K. Hintzer, B. Koppenhoefer, V. Schurig, J. Org. Chem. 1982, 47, 3850.
18. P. H. Dussault, T. K. Trullinger, F. Noor-e-Ain, Org. Lett. 2002, 4, 4591.
19. E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 1965, 87, 1353.
20. A review on heterobimetallic asymmetric catalysis: a) M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187;
21. For selected recent examples, see: b) N. Yamagiwa, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 16178;
22. c) N. Yamagiwa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2004, 116, 4593;
23. Angew. Chem. Int. Ed. 2004, 43, 4493;
24. d) N. Yamagiwa, H. Qin, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 13419.
25. General review for nonenzymatic kinetic resolution: E. Vedejs, M. Jure, Angew. Chem. 2005, 117, 4040;
26. Angew. Chem. Int. Ed. 2005, 44, 3974.
27. Kinetic resolution of 2,2-disubstituted terminal epoxides using a chiral metal catalyst is rare. For resolution with an azide nucleophile catalyzed by a (salen)Cr complex, see: a) H. Lebel, E. N. Jacobsen, Tetrahedron Lett. 1999, 40, 7303;
28. for reviews on biocatalytic kinetic resolutions, see: b) A. Steinreiber, K. Faber, Curr. Opin. Biotechnol. 2001, 12, 552;
29. c) A. Archelas, R. Furstoss, Curr. Opin. Chem. Biol. 2001, 5, 112.
30. Examples of kinetic resolution using heterobimetallic complexes: a) S.-y. Tosaki, K. Hara, V. Gnanadesikan, H. Morimoto, S. Harada, M. Sugita, N. Yamagiwa, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 11776;
31. b) H. Mihara, Y. Sohtome, S. Matsunaga, M. Shibasaki, Chem. Asian J. 2008, 3, 359.
32. Racemic synthesis of oxetane from ketones through the sequential addition of in situ generated sulfur ylides was reported. Oxirane ring-expansion reactions proceeded in tBuOH at 50 °C without any promoter, but no reaction proceeded in THF neither at 45°C nor at 50°C in the absence of (S)-1a. K. Okuma, Y. Tanaka, S. Kaji, H. Ohta, J. Org. Chem. 1983, 48, 5133. See also reference [4c] for oxirane ring-expansion with an ylide using a chiral 2-monosubstituted epoxide.
33. Reviews: a) E. M. Vogl, H. Gröger, M. Shibasaki, Angew. Chem. 1999, 111, 1672;
34. Angew. Chem. Int. Ed. 1999, 38, 1570;
35. b) M. Shibasaki, S. Matsunaga, N. Kumagai, Synlett 2008, 1583.
36. H. Kakei, T. Sone, Y. Sohtome, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 13410.
37. T. Sone, A. Yamaguchi, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2008, 130, 10078.
38. Steric and electronic modification of achiral phosphine oxides have beneficial effects in other rare-earth-metal-catalyzed asymmetric reactions: a) K. Daikai, M. Kamaura, J. Inanaga, Tetrahedron Lett. 1998, 39, 7321;
39. b) R. Kino, K. Daikai, T. Kawanami, H. Furuno, J. Inanaga, Org. Biomol. Chem. 2004, 2, 1822;
40. c) J. Tian, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2002, 114, 3788;
41. Angew. Chem. Int. Ed. 2002, 41, 3636;
42. d) N. Yamagiwa, J. Tian, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 3413;
43. e) H. Kakei, R. Tsuji, T. Ohshima, H. Morimoto, S. Matsunaga, M. Shibasaki, Chem. Asian J. 2007, 2, 257;
44. f) K. Hara, S.-Y. Park, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Chem. Asian J. 2008, 3, 1500;
45. g) H. Morimoto, T. Yoshino, T. Yukawa, G. Lu, S. Matsunaga, M. Shibasaki, Angew. Chem. 2008, 120, 9265;
46. Angew. Chem. Int. Ed. 2008, 47, 9125.
47. rel values. For discussion on the validity of the calculated values, see: J. M. Keith, J. F. Larrow, E. N. Jacobsen, Adv. Synth. Catal. 2001, 343, 5. See also Ref. [8]. In Table 1, the observed ee value of recovered epoxide 2a was lower than expected on the basis of the ee value of oxetane 4a, possibly because of side reaction from (R)-2a.
48. Alternatively, both the epoxidation and the ring-expansion reaction can be performed simultaneously at 45 °C. The reaction of acetophenone (6a) at 45 °C using 2.2 equivalents of ylide 3 and 20 mol% (S)-LLB from the beginning afforded oxetane 4a in slightly lower yield (70%yield) than that of entry 1 in Table 2, but in excellent enantioselectivity (99%ee) after 72 hours. The slightly lower yield and high ee value implied that chiral amplification worked nicely even though the enantiomeric excess of the intermediate epoxide was a little bit lower than the sequential process in Table 2.
49. The use of ethyl ketones is difficult at the moment because of their low reactivity in the second ring-expansion reaction and insufficient chiral amplification. For example, the reaction of propiophenone using 20 mol % of (S)-LLB at room temperature gave the intermediate epoxide in 88% ee. The subsequent ring-expansion reaction, however, gave the oxetane in only 26% yield and 91% ee. (Chemical Equation Presented)