Pure and Applied Chemistry

Pure Appl. Chem., 2010, Vol. 82, No. 7, pp. 1461-1469

http://dx.doi.org/10.1351/PAC-CON-09-09-10

Published online 2010-05-04

Highly enantioselective isomerization of primary allylic alcohols catalyzed by (P,N)-iridium complexes

References

• 1. S. Akutagawa. Comprehensive Asymmetric Catalysis, Vol. 2, E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Chap. 23, Springer, Berlin (1999).
• 2. S. Inoue, H. Takaya, K. Tani, S. Otsuka, T. Sato, R. Noyori. J. Am. Chem. Soc. 112, 4897 (1990). (http://dx.doi.org/10.1021/ja00168a040)
• 3. S. Akutagawa. Comprehensive Asymmetric Catalysis, Vol. 3, E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Chap. 41.4, Springer, Berlin (1999).
• 4a. R. C. Van der Drift, E. Bouwman, E. Drent. J. Organomet. Chem. 650, 1 (2002). (http://dx.doi.org/10.1016/S0022-328X(02)01150-6)
• 4b. R. Uma, C. Crévisy, R. Grée. Chem. Rev. 103, 27 (2003). (http://dx.doi.org/10.1021/cr0103165)
• 4c. V. Cadierno, P. Crochet, J. Gimeno. Synlett 8, 1105 (2008).
• 4d. for Rh-catalyzed asymmetric isomerization of primary allylic alcohols, see: C. Botteghi, G. Giacomelli. Gazz. Chim. Ital. 106, 1131 (1976).
• 4e. K. Tanaka, S. Qiao, M. Tobisu, M. M.-C. Lo, G. C. Fu. J. Am. Chem. Soc. 122, 9870 (2000). (http://dx.doi.org/10.1021/ja002471r)
• 4f. K. Tanaka, G. C. Fu. J. Org. Chem. 66, 8177 (2001). (http://dx.doi.org/10.1021/jo010792v)
• 4g. C. Chapuis, M. Barthe, J.-Y. de Saint Laumer. Helv. Chim. Acta 84, 230 (2001). (http://dx.doi.org/10.1002/1522-2675(20010131)84:1<230::AID-HLCA230>3.0.CO;2-V)
• 4h. F. Boeda, P. Mosset, C. Crévisy. Tetrahedron Lett. 47, 5021 (2006). (http://dx.doi.org/10.1016/j.tetlet.2006.05.108)
• 4i. for Ru-catalyzed asymmetric isomerization of secondary allylic alcohols, see: M. Ito, S. Kitahara, T. Ikariya. J. Am. Chem. Soc. 127, 6172 (2005). (http://dx.doi.org/10.1021/ja050770g)
• 5a. R. H. Crabtree, M. W. Davis. Organometallics 2, 681 (1983). (http://dx.doi.org/10.1021/om00077a019)
• 5b. R. H. Crabtree, M. W. Davis. J. Org. Chem. 51, 2655 (1986). (http://dx.doi.org/10.1021/jo00364a007)
• 6. G. Stork, D. Kahne. J. Am. Chem. Soc. 105, 1072 (1983). (http://dx.doi.org/10.1021/ja00342a080)
• 7a. D. A. Evans, L. Kværnø, T. B. Dunn, A. Beauchemin, B. Raymer, J. A. Mulder, E. J. Olhava, M. Juhl, K. Kagechika, D. A. Favor. J. Am. Chem. Soc. 130, 16285 (2008).
• 7b. S. Gao, Q. Wang, C. Chen. J. Am. Chem. Soc. 131, 1410 (2009). (http://dx.doi.org/10.1021/ja808110d)
• 7c. C. Fehr, I. Farris. Angew. Chem., Int. Ed. 45, 6904 (2006). (http://dx.doi.org/10.1002/anie.200602879)
• 8. L. Mantilli, C. Mazet. Tetrahedron Lett. 50, 4141 (2009). (http://dx.doi.org/10.1016/j.tetlet.2009.04.130)
• 9. A. Lightfoot, P. Schnider, A. Pfaltz. Angew. Chem., Int. Ed. 37, 2897 (1998). (http://dx.doi.org/10.1002/(SICI)1521-3773(19981102)37:20<2897::AID-ANIE2897>3.0.CO;2-8)
• 10. X. Li, L. Kong, Y. Gao, X. Wang. Tetrahedron Lett. 48, 3915 (2007). (http://dx.doi.org/10.1016/j.tetlet.2007.03.106)
• 11. J. W. Faller, S. C. Milheiro, J. Parr. J. Organomet. Chem. 691, 4945 (2006). (http://dx.doi.org/10.1016/j.jorganchem.2006.08.032)
• 12. S. Kaiser, S. P. Smidt, A. Pfaltz. Angew. Chem., Int. Ed. 45, 5194 (2006). (http://dx.doi.org/10.1002/anie.200601529)
• 13. J. Sprinz, G. Helmchen. Tetrahedron Lett. 34, 1769 (1993). (http://dx.doi.org/10.1016/S0040-4039(00)60774-8)
• 14. H. Danjo, M. Higuchi, M. Yada, T. Imamaoto. Tetrahedron Lett. 45, 603 (2004). (http://dx.doi.org/10.1016/j.tetlet.2003.10.160)
• 15. M. G. Schrems, E. Neumann, A. Pfaltz. Angew. Chem., Int. Ed. 46, 8274 (2007). (http://dx.doi.org/10.1002/anie.200702555)
• 16. L. Mantilli, D. Gérard, S. Torche, C. Besnard, C. Mazet. Angew. Chem., Int. Ed. 48, 5143 (2009). (http://dx.doi.org/10.1002/anie.200901863)
• 17. CCDC-724940. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via <www.ccdc.cam.ac.uk/data_request/cif>.
• 18. The tautomerization is presumably taking place outside the catalytic cycle, since attempts to isomerize 2,3-disubstituted allylic alcohols gave the corresponding α-substituted aldehydes in racemic form. The tautomerization is the enantio-determining step for 2,3-disubstituted allylic alcohols. If the metal is not involved or if background tautomerization is too fast, racemic product is expected. For a relevant discussion, see: S. Bergens, B. Bosnich. J. Am. Chem. Soc. 113, 958 (1991). (http://dx.doi.org/10.1021/ja00003a032)