Pure and Applied Chemistry

Pure Appl. Chem., 2011, Vol. 83, No. 3, pp. 577-585

http://dx.doi.org/10.1351/PAC-CON-10-09-23

Published online 2011-01-31

Rhodium-catalyzed enantioselective intermolecular hydroacylation reactions

References

• 1a. M. T. Reetz. In Stereocontrolled Organic Synthesis, B. M. Trost (Ed.), Blackwell Science, Oxford (1994).
• 1b. M. T. Reetz. In Catalytic Asymmetric Synthesis, 2^nd ed., I. Ojima (Ed.), Wiley-VCH, New York (2000).
• 2a. M. C. Willis. Chem. Rev. 110, 725 (2010). (http://dx.doi.org/10.1021/cr900096x)
• 2b. C.-H. Jun, E.-A. Jo, J.-W. Park. Eur. J. Org. Chem. 1869 (2007). (http://dx.doi.org/10.1002/ejoc.200600846)
• 3a. J. W. Suggs. J. Am. Chem. Soc. 100, 640 (1978). (http://dx.doi.org/10.1021/ja00470a054)
• 3b. K. P. Vora, C. F. Lochow, R. G. Miller. J. Organomet. Chem. 192, 257 (1980). (http://dx.doi.org/10.1016/S0022-328X(00)94430-9)
• 3c. K. Kokubo, K. Matsumasa, Y. Nishinaka, M. Miura, M. Nomura. Bull. Chem. Soc. Jpn. 72, 303 (1999). (http://dx.doi.org/10.1246/bcsj.72.303)
• 3d. C.-H. Jun, D.-Y. Lee, H. Lee, J.-B. Hong. Angew. Chem., Int. Ed. 39, 3070 (2000).
• 3e. C.-H. Jun, H. Lee, J.-B. Hong, B.-I. Kwon. Angew. Chem., Int. Ed. 41, 2146 (2002). (http://dx.doi.org/10.1002/1521-3773(20020617)41:12<2146::AID-ANIE2146>3.0.CO;2-2)
• 3f. C.-H. Jun, H. Lee. Pure Appl. Chem. 76, 577 (2004). (http://dx.doi.org/10.1351/pac200476030577)
• 3g. M. Imai, M. Tanaka, K. Tanaka, Y. Yamamoto, N. Imai-Ogata, M. Shimowatari, S. Nagumo, N. Kawahara, H. Suemune. J. Org. Chem. 69, 1144 (2004). (http://dx.doi.org/10.1021/jo035395u)
• 3h. T. Tanaka, M. Tanaka, H. Suemune. Tetrahedron Lett. 46, 6053 (2005). (http://dx.doi.org/10.1016/j.tetlet.2005.07.004)
• 3i. K. Tanaka, Y. Shibata, T. Suda, Y. Hagiwara, M. Hirano. Org. Lett. 9, 1215 (2007). (http://dx.doi.org/10.1021/ol070153s)
• 4. Methods without chelation control have also been described, see.
• 4a. P. Isnard, B. Denise, R. P. A. Sneeden, J. M. Cognion, P. Durual. J. Organomet. Chem. 240, 285 (1982). (http://dx.doi.org/10.1016/S0022-328X(00)86794-7)
• 4b. T. B. Marder, D. C. Roe, D. Milstein. Organometallics 7, 1451 (1988). (http://dx.doi.org/10.1021/om00096a037)
• 4c. T. Kondo, M. Akazome, Y. Tsuji, Y. Watanabe. J. Org. Chem. 55, 1286 (1990). (http://dx.doi.org/10.1021/jo00291a035)
• 4d. C. P. Lenges, P. S. White, M. Brookhart. J. Am. Chem. Soc. 120, 6965 (1998). (http://dx.doi.org/10.1021/ja980610n)
• 4e. Y.-T. Hong, A. Barchuk, M. J. Krische. Angew. Chem., Int. Ed. 45, 6885 (2006). (http://dx.doi.org/10.1002/anie.200602377)
• 4f. A. H. Roy, C. P. Lenges, M. Brookhart. J. Am. Chem. Soc. 129, 2082 (2007). (http://dx.doi.org/10.1021/ja066509x)
• 4g. S. Omura, T. Fukuyama, J. Horiguchi, Y. Murakami, I. Ryu. J. Am. Chem. Soc. 130, 14094 (2008). (http://dx.doi.org/10.1021/ja806929y)
• 4h. F. Shibahara, J. F. Bower, M. J. Krische. J. Am. Chem. Soc. 130, 14120 (2008). (http://dx.doi.org/10.1021/ja805356j)
• 4i. V. M. Williams, J. C. Leung, R. L. Patman, M. J. Krische. Tetrahedron 65, 5024 (2009). (http://dx.doi.org/10.1016/j.tet.2009.03.068)
• 5a. M. C. Willis, S. Sapmaz. Chem. Commun. 2558 (2001). (http://dx.doi.org/10.1039/b107852f)
• 5b. M. C. Willis, S. J. McNally, P. J. Beswick. Angew. Chem., Int. Ed. 43, 340 (2004). (http://dx.doi.org/10.1002/anie.200352751)
• 5c. M. C. Willis, R. L. Woodward. J. Am. Chem. Soc. 127, 18012 (2005). (http://dx.doi.org/10.1021/ja056130v)
• 5d. M. C. Willis, H. E. Randell-Sly, R. L. Woodward, S. J. McNally, G. S. Currie. J. Org. Chem. 71, 5291 (2006). (http://dx.doi.org/10.1021/jo060582o)
• 5e. G. L. Moxham, H. E. Randell-Sly, S. K. Brayshaw, R. L. Woodward, A. S. Weller, M. C. Willis. Angew. Chem., Int. Ed. 45, 7618 (2006). (http://dx.doi.org/10.1002/anie.200603133)
• 5f. G. L. Moxham, H. Randell-Sly, S. K. Brayshaw, A. S. Weller, M. C. Willis. Chem.—Eur. J. 14, 8383 (2008). (http://dx.doi.org/10.1002/chem.200800738)
• 5g. J. D. Osborne, M. C. Willis. Chem. Commun. 5025 (2008). (http://dx.doi.org/10.1039/b810935d)
• 6. M. C. Willis, H. E. Randell-Sly, R. L. Woodward, G. S. Currie. Org. Lett. 7, 2249 (2005). (http://dx.doi.org/10.1021/ol050638l)
• 7a. B. R. James, C. G. Young. J. Chem. Soc., Chem. Comm. 1215 (1983). (http://dx.doi.org/10.1039/c39830001215)
• 7b. B. Bosnich. Acc. Chem. Res. 31, 667 (1998), and references therein. (http://dx.doi.org/10.1021/ar970095i)
• 7c. M. Tanaka, M. Imai, M. Fujio, E. Sakamoto, M. Takahashi, Y. Eto-Kato, X. M. Wu, K. Funakoshi, K. Sakai, H. Suemune. J. Org. Chem. 65, 5806 (2000), and references therein. (http://dx.doi.org/10.1021/jo000781m)
• 7d. K. Kundu, J. V. McCullagh, A. T. Morehead Jr. J. Am. Chem. Soc. 127, 16042 (2005). (http://dx.doi.org/10.1021/ja0564416)
• 7e. M. M. Coulter, P. K. Dornan, V. M. Dong. J. Am. Chem. Soc. 131, 6932 (2009). (http://dx.doi.org/10.1021/ja901915u)
• 8a. X. M. Wu, K. Funakoshi, K. Sakai. Tetrahedron Lett. 33, 6331 (1992). (http://dx.doi.org/10.1016/S0040-4039(00)60966-8)
• 8b. R. W. Barnhart, X. Wang, P. Noheda, S. H. Bergens, J. Whelan, B. Bosnich. J. Am. Chem. Soc. 116, 1821 (1994). (http://dx.doi.org/10.1021/ja00084a025)
• 9. K. Tanaka, G. Fu. J. Am. Chem. Soc. 124, 10246 (2002).
• 10. K. Tanaka, G. Fu. J. Am. Chem. Soc. 125, 8078 (2003). (http://dx.doi.org/10.1021/ja035489l)
• 11. See refs. [3g–i] and [4c–i] for examples that include disubstituted alkenes.
• 12. R. T. Stemmler, C. Bolm. Adv. Synth. Catal. 349, 1185 (2007). (http://dx.doi.org/10.1002/adsc.200600583)
• 13. Y. Inui, M. Tanaka, M. Imai, K. Tanaka, H. Suemune. Chem. Pharm. Bull. 57, 1158 (2009). (http://dx.doi.org/10.1248/cpb.57.1158)
• 14. Y. Shibata, K. Tanaka. J. Am. Chem. Soc. 131, 12552 (2009). (http://dx.doi.org/10.1021/ja905908z)
• 15. See ref. [3i].
• 16. J. D. Osborne, H. E. Randell-Sly, G. S. Currie, A. R. Cowley, M. C. Willis. J. Am. Chem. Soc. 130, 17232 (2008). (http://dx.doi.org/10.1021/ja8069133)
• 17. For a non-asymmetric hydroacylation employing allenes, see.
• 17a. ref. [3c].
• 17b. H. E. Randell-Sly, J. D. Osborne, R. L. Woodward, G. S. Currie, M. C. Willis. Tetrahedron 65, 5110 (2009). (http://dx.doi.org/10.1016/j.tet.2009.03.054)
• 18. C. González-Rodríguez, S. R. Parsons, A. L. Thompson, M.C. Willis. Chem.—Eur. J. 16, 10950 (2010). (http://dx.doi.org/10.1002/chem.201001748)
• 19a. E. Vedejs, M. Jure. Angew. Chem., Int. Ed. 44, 3974 (2005). (http://dx.doi.org/10.1002/anie.200460842)
• 19b. J. M. Keith, J. F. Larrow, E. N. Jacobsen. Adv. Synth. Catal. 343, 5 (2001). (http://dx.doi.org/10.1002/1615-4169(20010129)343:1<5::AID-ADSC5>3.0.CO;2-I)
• 19c. A. H. Hoveyda, M. T. Didiuk. Curr. Org. Chem. 2, 537 (1998).
• 19d. H. B. Kagan, J. C. Fiaud. In Topics in Stereochemistry, E. L. Eliel, J. C. Fiaud (Eds.), Vol. 18, p. 249, John Wiley, New York (1988).
• 20. D. H. T. Phan, B. Kim, V. M. Dong. J. Am. Chem. Soc. 131, 15608 (2009). (http://dx.doi.org/10.1021/ja907711a)
• 21a. M. Chérest, H. Felkin, N. Prudent. Tetrahedron Lett. 9, 2199 (1968). (http://dx.doi.org/10.1016/S0040-4039(00)89719-1)
• 21b. A. Mengel, O. Reiser. Chem. Rev. 99, 1191 (1999). (http://dx.doi.org/10.1021/cr980379w)
• 22. C. R. Sarko, I. C. Guch, M. DiMare. J. Org. Chem. 59, 705 (1994). (http://dx.doi.org/10.1021/jo00083a004)
• 23. While this manuscript was in the proof stage, two reports from the Dong group describing new enantioselective intermolecular hydroacylations appeared.
• 23a. M. M. Coulter, K. G. M. Kou, B. Galligan, V. M. Dong. J. Am. Chem. Soc. 132, 16330 (2010). (http://dx.doi.org/10.1021/ja107198e)
• 23b. D. H. T. Phan, K. G. M. Kou, V. M. Dong. J. Am. Chem. Soc. 132, 16354 (2010). (http://dx.doi.org/10.1021/ja107738a)