Asymmetric reductions using the chiral boronic ester TarB-H: a practical and inexpensive procedure for synthesizing chiral alcohols

Tetrahedron Letters

Volumn 48, Issue 51, 2007, Pages 9025-9029

  Eagon, Scott ^a   Kim, Jinsoo ^a   Yan, Katie ^a   Haddenham, Dustin ^a   Singaram, Bakthan ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Acyloxyborohydride; Asymmetric reduction; Sodium borohydride; TarB X

Indexed keywords

ALCOHOL DERIVATIVE; BENZENEBORONIC ACID; BORON; ESTER; ETHER; KETONE DERIVATIVE; SODIUM BOROHYDRIDE; TARTARIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; EXTRACTION; NUCLEAR MAGNETIC RESONANCE; REDUCTION; SYNTHESIS;

EID: 36248962688     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.075     Document Type: Article

References (35)

1. In: Morrison J.D. (Ed). Asymmetric Synthesis (1983), Academic Press, New York Vol. 2, Chapters 2 and 3
2. Corey E.J., Bakshi R.K., and Shibata S. J. Am. Chem. Soc. 109 (1987) 5551-5553
3. Hong Y., Gao Y., Nie X., and Zepp C.M. Tetrahedron Lett. 35 (1994) 6631-6634
4. Quallich G.J., and Woodall T.M. Synlett (1993) 929-930
5. Berenguer R., Garcia J., and Vilarrasa J. Tetrahedron: Asymmetry 5 (1994) 165-168
6. Brown H.C., Chandreskharan J., and Ramachandran P.V. J. Am. Chem. Soc. 110 (1988) 1539-1546
7. Umino N., Iwakuma T., and Itoh N. Chem. Pharm. Bull. 27 (1979) 1479-1481
8. Yamada K., Takeda M., and Iwakuma T. J. Chem. Soc., Perkin Trans. 1 (1983) 265-270
9. Hirao A., Nakahama S., Mochizuki D., Itsuno S., Ohaowa M., and Yamazaki N. J. Chem. Soc., Chem. Commun. (1979) 807-808
10. Hirao A., Mochizuki H., Nakahama S., and Yamazaki N. J. Org. Chem. 44 (1979) 1720-1722
11. Hirao A., Itsuno S., Mochizuki H., Nakahara S., and Yamazaki N. Bull. Chem. Soc. Jpn. 54 (1981) 1424-1428
12. Colonna S., and Fornasier R. J. Chem. Soc., Perkin Trans. 1 (1978) 371-373
13. Nagata T., Yorozu K., Yamada T., and Mukaiyama T. Angew. Chem., Int. Ed. Engl. 34 (1995) 2145-2147
14. Sugi K.D., Nagata T., Yamada T., and Mukaiyama T. Chem. Lett. (1997) 493-494
15. Yamada T., Nagata T., Sugi K.D., Yorozu K., Ikeno T., Ohtsuka Y., Miyazaki D., and Mukaiyama T. Chem. Eur. J. 9 (2003) 4485-4509
16. Hirao A., Nakahama S., Mochizuki H., Itsuno S., and Yamazaki N. J. Org. Chem. 45 (1980) 4231-4233
17. Hirao A., Itsuno M., Owa M., Nagami S., Moxhizuki H., Zoorov H.H.A., Niakahama S., and Yamazaki N. J. Chem. Soc., Perkin Trans. 1 (1981) 900-905
18. Morrison J.D., Grandbois E.R., and Howard S.I. J. Org. Chem. 45 (1980) 4229-4231
19. Nasipuri D., Sarkar A., Konar S.K., and Ghosh A. Indian J. Chem., Sect. B 21 (1982) 212-215
20. Bianchi G., Achilli F., Gamba A., and Vercesi D. J. Chem. Soc., Perkin Trans. 1 (1988) 417-422
21. Adams C. Synth. Commun. 14 (1984) 955-959
22. Hirao A., Mochizuki H., Zoorob H.H.A., Igarashi I., Itsuno S., Ohwa M., Nakahama S., and Yamazaki N. Agric. Biol. Chem. 45 (1981) 693-697
23. Yatagai M., and Ohnuki T. J. Chem. Soc., Perkin Trans. 1 (1990) 1826-1828
24. Iwagami H., Yatagai M., Nakazawa H., Orita H., Honda Y., Ohnuki T., and Yukawa T. Bull. Chem. Soc. Jpn. 64 (1991) 175-182
25. Polyak F.D., Solodin I.V., and Dorofeeva T.V. Synth. Commun. 21 (1991) 1137-1142
26. Suri J.T., Vu T., Hernandez A., Congdon J., and Singaram B. Tetrahedron Lett. 43 (2002) 3649-3652
27. Cordes D.B., Kwong T.J., Morgan K.A., and Singaram B. Tetrahedron Lett. 47 (2006) 349-351
28. Gribble G.W. Chem. Soc. Rev. 27 (1998) 395
29. Kim J., and Singaram B. Tetrahedron Lett. 47 (2006) 3901-3903
30. Cordes D.B., Nguyen T.M., Kwong T.J., Suri J.T., Luibrand R.T., and Singaram B. Eur. J. Org. Chem. (2005) 5289-5295
31. Fu X., McAlister T.L., Thiruvengadam T.K., Tann C.H., and Su D. Tetrahedron Lett. 44 (2003) 801-804
32. Brown H.C., and Ramachandran P.V. Acc. Chem. Res. 25 (1992) 16-24
33. Phenylboronic acid costs approximately $430/mol, 4-fluorophenylboronic acid $1400/mol, 4-chlorophenylboronic acid $1,500/mol, and 3-nitrophenylboronic acid $1600/mol.
34. 2 gas.
35. 4. Evaporation under reduced pressure yielded the product alcohol. The enantiomeric excess of the acetylated alcohol was determined by GC on a Supelco β-cyclodextrin 120 column (30 m × 0.25 mm). For the α-haloacetophenone derivatives, the product epoxide was run without further modification through the GC.