Overman rearrangement of γ-aryl crotyl alcohols: Effects of aryl substituents

Synthetic Communications

Volumn 30, Issue 9, 2000, Pages 1643-1650

  Cho, Cheon Gyu ^a   Lim, Yeong Kwan ^a   Lee, Kang Sang ^a   Jung, In Hak ^a   Yoon, Moon Yeong ^a  

^a Hanyang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; KINETICS; REACTION ANALYSIS; SYNTHESIS;

EID: 0034119149     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397910008087201     Document Type: Article

References (16)

1. Overman, L. E. J. Am. Chem. Soc. 1974, 96, 597-599.
2. For recent references, see: (a) Nishikawa, T.; Asai, M.; Ohyabu, N. and Isobe, M. J. Org. Chem. 1998, 63, 188-192.
3. (b) Imogai, H.; Petit, Y. and Larcheveque, M. Tetrahedron Lett. 1996, 37, 2573-2576.
4. Takeda, K.; Kaji, E.; Nakamura, H.; Akiyama, A.; Konda, Y.; Mizuno, Y.; Takayanagi, H. and Harigaya, Y. Synthesis 1996, 341-348.
5. Chida, N.; Tsutsumi, N. and Ogawa, S. J. Chem. Soc., Chem. Commun. 1995, 793-794.
6. For reviews, see: (a) Ritter, K. "Houben-Weyl. Stereoselective Synthesis," E 21, Vol. 9; Helmechen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme, Stuttgart, 1996; pp. 5677-5699.
7. (b) Overman, L. E. Acc. Chem. Res. 1980, 13, 218-224.
8. Doherty, A. M.; Kornberg, B. E. and Reily, M. D. J. Org. Chem. 1993, 58, 795-798.
9. (a) Donde, Y. and Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933-2934.
10. (b) Cohen, F. and Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222.
11. (a) Barbot, F. and Miginiac, L. Synth. Comm. 1997, 27, 2601-2614.
12. (b) Kolasa, T.; Sharma, S. and Miller, M. J. Tetrahedron Lett. 1987, 28, 4973-4976.
13. Nesi, M.; Brasca, M. G.; Longo, A.; Moretti, W. and Panzeri, A. Tetrahedron Lett. 1997, 38,4881-4884.
14. Overman, L. E. and Zipp, G. G. J. Org. Chem. 1997, 62, 2288-2291.
15. Isobe's procedure (ref. 2a) was used with a few modifications, due to the acid sensitiveness of the intermediate allylic trichloroacetimidates, see the experimental section for details.
16. Berkowitz, D. B.; Pedersen, M. L. and Jahng, W.-J. Tetrahedron Lett. 1996, 37, 4309-4312 and references cited therein.