Catalytic asymmetric intramolecular allylation of aldehyde

Heterocycles

Volumn 77, Issue 1, 2009, Pages 587-593

  Sato, Tomohiro ^a   Tomioka, Kiyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Allylation; Asymmetric Reaction; Catalytic Reaction; Intramolecular Reaction; Pyrrolidine

Indexed keywords

EID: 65549099061     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(F)19     Document Type: Article

References (18)

1. Kuriyama M., Soeta T., Hao X., Chen Q., and Tomioka K. J. Am. Chem. Soc. 126 (2004) 8128
2. Soeta T., Kuriyama M., and Tomioka K. J. Org. Chem. 70 (2005) 297
3. Chen Q., Soeta T., Kuriyama M., Yamada K., and Tomioka K. Adv. Synth. Catal. 348 (2006) 2604
4. Tomioka K. Pure Appl. Chem. 78 (2006) 2029
5. Soeta T., Selim K., Kuriyama M., and Tomioka K. Tetrahedron 63 (2007) 6573
6. Soeta T., Selim K., Kuriyama M., and Tomioka K. Adv. Synth. Catal. 349 (2007) 629
7. Selim K., Soeta T., Yamada K., and Tomioka K. Chem. Asian J. 3 (2008) 342
8. In: Dalko P.I. (Ed). Enantioselective Organocatalysis: Reactions and Experimental Procedures (2007), Wiley-VCH, Weinheim
9. Mukherjee S., Yang J.W., Hoffmann S., and List B. Chem. Rev. 107 (2007) 5471
10. Hiroi K., and Abe J. Tetrahedron Lett. 31 (1990) 3623
11. Efficient intramolecular asymmetric alkylation instead of allylation of aldehyde has been reported. Vignola N., and List B. J. Am. Chem. Soc. 126 (2004) 450
12. Allylation of carbonyl compounds has been reported recently. Ibrahem I., and Córdova A. Angew. Chem. Int. Ed. 45 (2006) 1952
13. Bihelovic F., Matovic R., Vulovic B., and Saicic R.N. Org. Lett. 9 (2007) 5063
14. Schmid G.A., and Borschberg H.-J. Helv. Chim. Acta 84 (2001) 388
15. The trans-stereochemistry was assigned to major 7 based on its behavior under acidic isomerization conditions. Kogen H., Tomioka K., Hashimoto S., and Koga K. Tetrahedron 37 (1981) 3951
16. The absolute configuration of 7 was not determined yet.
17. Scholl M., Ding S., Lee C.W., and Grubbs R.H. Org. Lett. 1 (1999) 953
18. Kingsbury J.S., Harrity J.P.A., Bonitatebus P.J., and Hoveyda A.H. J. Am. Chem. Soc. 121 (1999) 791