Catalytic enantioselective intermolecular hydroacylation: Rhodium-catalyzed combination of β-S-aldehydes and 1,3-disubstituted allenes

Journal of the American Chemical Society

Volumn 130, Issue 51, 2008, Pages 17232-17233

  Osborne, James D ^a   Randell Sly, Helen E ^b   Currie, Gordon S ^c   Cowley, Andrew R ^a   Willis, Michael C ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b University of Bath Claverton Down   (United Kingdom)

^c ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENES; ENANTIOSELECTIVE; GOOD YIELD; HIGH ENANTIOSELECTIVITY; HYDROACYLATION; NONCONJUGATED; RHODIUM-CATALYZED;

ENANTIOSELECTIVITY; RHODIUM;

ALDEHYDES;

ALDEHYDE; ALLENE DERIVATIVE; LIGAND; RHODIUM; ALKENE; CARBON; METAL;

ACYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; CHIRALITY; CONTROLLED STUDY; ELECTRON; ENANTIOMER; ENANTIOSELECTIVITY; RACEMIZATION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; STEREOISOMERISM; TEMPERATURE;

ALDEHYDES; ALKENES; CARBON; CATALYSIS; CHEMISTRY; LIGANDS; METALS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; RHODIUM; STEREOISOMERISM; TEMPERATURE;

EID: 67749120520     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8069133     Document Type: Article

References (42)

1. Sakai, K.; He, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 1287.
2. Selected examples: (a) Fairlie, D. P.: Bosnich. B. Qrganometallics 1988, 7, 936.
3. (b) Fairlie. D. P.; Bosnich, B. Organometallics 1988, 7, 946.
4. Gable. K. P.; Benz, G. A. Tetrahedron Lett 1991, 32, 3473.
5. Sattelkau, T.; Eilbraeht, P. Tetrahedron Lett. 1998, 39, 9647.
6. (e) Morgan, J. P.; Kundu, K.; Doyle, M. P. Chem. Commun. 2005, 3307.
7. Selected examples: (a) James, B. R.; Young. C. G. J. Chem. Soc., Chem. Commun. 1983, 1215.
8. (b) Bosnich, B. Acc. Chem. Res. 1998, 31, 667, and references therein,
9. Tanaka. M.; Imai. M.; Fujio, M.; Sakamoto, E.; Takahashi, M.; Eto-Kato, Y.; Wu, X. M.; Funakoshi, K.; Sakai, K; Suemune, H. J. Org. Chem. 2000. 65, 5806, and references therein.
10. Kundu. K.; McCullagh. J. V.; Morehead, A. T., Jr. J. Am. Chem. Soc. 2005, 127, 16042.
11. Examples: (a) Schwartz. J.; Cannon. J. B. J. Am. Chem. Soc. 1974. 96, 4721.
12. (b) Vora, K. P.; Lochow. C. R; Miller. R. G. J. Organomet. Chem. 1980, 192, 257.
13. Marder. T. B.; Roe. D. C.; Milstein. D. Orsanometallics 1988, 7, 1451.
14. Kondo, T.; Tsuji. Y.; Watanabe, Y. Tetrahedron Lett. 1987, 28, 6229.
15. (e) Lenges. C. P.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 6965.
16. (f) Rov. A. H.; Lenges. C. P.: Brookhart. M. J. Am. Chem. Soc. 2007. 129, 2082.
17. (g) Shibahara, F.; Bower, J. F.; Krische. M. J. J. Am. Chem. Soc. 2008, 130, 14120.
18. (h) Omura, S.; Fukuvama, T.; Horiguchi. J.; Murakami. Y.; Rvu. I. J. Am. Chem. Soc. 2008, 130, 14094.
19. (a) Suggs, J. W. J.,4m. Chem. Soc. 1978, 100, 640.
20. (b) Jun, C.-H.; Lee, D.-Y.; Lee, H.; Hons, J.-B. Angew. Chem. Int. Ed. 2000, 39, 3070.
21. Park, Y. J.; Park, J.-W; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222.
22. Imai, M.; Tanaka, M.; Tanaka, K.; Yamamoto, Y.; Imai-Ogata, N.; Shimowatari, M.; Naeumo, S.: Kawahara, N.; Suemune, H. J. Org. Chem. 2004, 69, 1144.
23. (e) Tanaka, T.; Tanaka. M.; Suemune. FT. Tetrahedron Lett. 2005, 46, 6053.
24. (f) Tanaka. K.; Shibata. Y.; Suda, T.; Hagiwara, Y.; Hirano, M. Org. Lett. 2007, 9, 1215.
25. For methods that do allow the use of substituted alkenes, see: refs 4d,f,g,h and 5d,e,f.
26. Stemmler, R. T.; Bolm, C. Adv. Synth. Catal. 2007, 349, 1185.
27. (a) Modern Allene Chemistry; Krause. N.; Hashmi, A. S. K., Eds.; Wilev- VCH: Weinheim, 2004.
28. (b) Ma, S. Chem. Rev. 2005, 105, 2829.
29. Selected recent examples: (a) Zhang. Z.; Bender. C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2007, 129, 14148.
30. (b) Burks, Ft. E.; Liu, S.; Morken. J. P. J. Am. Chem. Soc. 2007, 129, 8766.
31. LaLonde. R. L.; Sherrv, B. D.; Kang. E. J.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 2452.
32. Trost, B. M.; Simas, A. B. C.; Plietker. B.; Jakel. C.; Xie, J. Chem.-Eur. J. 2005, 11, 7075.
33. Kokubo. K.; Matsumasa, K.; Nishinaka. Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1999, 72, 303.
34. (a) Willis, M. C.; McNallv, J. S.; Beswick, P. J. Angew. Chem., Int. Ed. 2004, 43, 340.
35. (b) Willis,'M. C.; Randell-Sly, H. E.; Woodward, R. L.; Currie. G. S. Org. Lett. 2005, 7. 2249.
36. Willis, M. C.; Randell-Slv. H. E.; Woodward. R. L.; McNallv. S. J.; Currie. G. S. J. Org. Chem. 2006, 71, 5291.
37. Moxham. G. L.; Randell-Sly, H. E.; Brayshaw, S. K.; Woodward. R. L.; Weller, A. S.; Willis, M. C. Angew. Chem., Int. Ed. 2006, 45, 7618 For an intramolecular example, see:
38. (e) Bendorf, Ft. D.; Colella, C. M.; Dixon. E. C.; Marchetti. M.; Matukonis, A. N.; Musselman, J. D.; Tiley, T. A. Tetrahedron Lett. 2002, 43, 7031.
39. Single regio- and geometrical isomers were observed in all cases.
40. Trialkyl-substituted allenes delivered no hydroacylation products when combined with aldehyde 9.
41. Both reactions illustrated in Scheme 1 were performed for 24 h. However, there was an observable difference in the rates of the two processes, with the (S,S)-catalyst delivering slower reactions. Comparative times to achieve 60% conversion: (R,R)-catalyst 11 h; (S,S)-catalyst 17 h.
42. We have established that there is no product racemization under the standard reaction conditions.