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An Efficient Synthesis of Chiral Alcohols via Catalytic Hydrogenation of Esters

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Abstract

A ruthenium complex was found to catalyze the hydrogenation of chiral esters without the loss of their optical purities under mild and neutral conditions. This method can avoid a violent quench step and an extraction step which accompany conventional reduction using metal hydride reagents such as sodium borohydride and lithium aluminum hydride.

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Notes

  1. Within our research, THF solvent performed better than other solvents. In addition, other types of esters such as isopropyl ester, benzyl ester and phenyl ester were not hydrogenated as effectively as methyl ester (Unpublished data)

References

  1. Farina V, Reeves JT, Senanayake CH, Song JJ (2006) Chem Rev 106:2734

    Article  CAS  Google Scholar 

  2. Noyori R, Ohkuma T (2001) Angew Chem Int Ed 40:40

    Article  CAS  Google Scholar 

  3. Noyori R (2002) Angew Chem Int Ed 41:2008

    Article  CAS  Google Scholar 

  4. Tang W, Zhang X (2003) Chem Rev 103:3029

    Article  CAS  Google Scholar 

  5. Shimizu H, Nagasaki I, Saito T (2005) Tetrahedron 61:5405

    Article  CAS  Google Scholar 

  6. Santaniello E, Ferraboschi P, Grisenti P, Manzocchi A (1992) Chem Rev 92:1071

    Article  CAS  Google Scholar 

  7. Bertschy H, Chenault HK, Whitesides GM (1995) In: Drauz K, Waldmann H (eds) Enzyme catalysis in organic synthesis a comprehensive handbook, vol II. Wiley-VCH, Weinheim, p 2227

    Google Scholar 

  8. Pàmies O, Bäckvall J–E (2003) Chem Rev 103:3247

    Article  Google Scholar 

  9. Studer M, Burkhardt S, Blaser H-U (2001) Adv Synth Catal 343:802

    Article  CAS  Google Scholar 

  10. Saudan LA, Saudan CM, Debieux C, Wyss P (2007) Angew Chem Int Ed 46:7473

    Article  CAS  Google Scholar 

  11. Doucet H, Ohkuma T, Murata K, Yokozawa T, Kozawa M, Katayama E, England AF, Ikariya T, Noyori R (1998) Angew Chem Int Ed 37:1703

    Article  CAS  Google Scholar 

  12. Ohkuma T, Koizumi M, Muñiz K, Hilt G, Kabuto C, Noyori R (2002) J Am Chem Soc 124:6508

    Article  CAS  Google Scholar 

  13. Xie J–H, Zhou Z–T, Kong W–L, Zhou Q–L (2007) J Am Chem Soc 129:1868

    Article  CAS  Google Scholar 

  14. Yamakawa M, Ito H, Noyori R (2000) J Am Chem Soc 122:1466

    Article  CAS  Google Scholar 

  15. Abdur-Rashid K, Clapham SE, Hadzovic A, Harvey JN, Lough AJ, Morris RH (2002) J Am Chem Soc 124:15104

    Article  CAS  Google Scholar 

  16. Sandoval CA, Ohkuma T, Muñiz K, Noyori R (2003) J Am Chem Soc 125:13490

    Article  CAS  Google Scholar 

  17. Hamilton RJ, Leong CG, Bigam G, Miskolzie M, Bergens SH (2005) J Am Chem Soc 127:4152

    Article  CAS  Google Scholar 

  18. Hadzovic A, Song D, MacLaughlin CM, Morris RH (2007) Organometallics 26:5987

    Article  CAS  Google Scholar 

  19. Hamilton RJ, Bergens SH (2008) J Am Chem Soc 130:11979

    Article  CAS  Google Scholar 

  20. Ohkuma T, Sandoval CA, Srinivasan R, Lin Q, Wei Y, Muñiz K, Noyori R (2005) J Am Chem Soc 127:8288

    Article  CAS  Google Scholar 

  21. Lindner E, Mayer HA, Warad I, Eichele K (2003) J Organomet Chem 665:176

    Article  CAS  Google Scholar 

  22. Guo R, Chen X, Elpelt C, Song D, Morris RH (2005) Org Lett 7:1757

    Article  CAS  Google Scholar 

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Correspondence to Yasunori Ino.

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Ino, Y., Kuriyama, W., Ogata, O. et al. An Efficient Synthesis of Chiral Alcohols via Catalytic Hydrogenation of Esters. Top Catal 53, 1019–1024 (2010). https://doi.org/10.1007/s11244-010-9573-x

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