Rate enhancing effect of hydrogen chloride and methanesulfonic acid on the intramolecular asymmetric reduction of o-aminoaceto- and -benzophenones with diisopinocampheylborane

Tetrahedron Letters

Volumn 38, Issue 6, 1997, Pages 957-960

  Ramachandran, P Veeraraghavan ^a   Malhotra, Sanjay V ^a   Brown, Herbert C ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; BENZYL ALCOHOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0031562031     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02489-6     Document Type: Article

References (16)

1. 1. Paper #101 presented at the 29th ACS Great Lakes Regional Meeting, Normal, IL, May 20, 1996.
2. 2. Postdoctoral Research Associate on a grant from the U. S. Army Research Office.
3. 3. Reductions in Organic Synthesis, Abdel-Magid, A. F.; Ed. American Chemical Society, Washington, DC, 1996.
4. 4. Brown, H. C.; Chandrasekharan, J.; Ramachandran, P. V. J. Am. Chem. Soc. 1988, 110, 1539. DIP-Chloride is a trademark of the Aldrich Chemical Company.
5. 5. Ramachandran, P. V.; Brown, H. C. in ref. 3. Chapter 5.
6. 6. Ramachandran, P. V.; Gong, B.; Brown, H. C. Tetrahedron Lett. 1994, 35, 2141.
7. 6 Shieh, W. C.; Cantrell, Jr., E. R.; Carlson, J. A. Tetrahedron Lett. 1995, 36, 3797.
8. 2BH by itself is not an efficient reducing agent. Brown, H. C.; Mandal, A. K. J. Org. Chem. 1977, 42, 2996.
9. 9. Ramachandran, P. V.; Chen, G. M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205.
10. 10. (a) Lockart, J. C. J. Chem. Soc. 1962, 1197.
11. (b) Cragg, R. H.; Miller, T. J. J. Organometal. Chem. 1982, 232, 201.
12. 11. A rate difference (10 min vs 12 d) in the reduction of 3a and 3b with sodium borohydride-acetic acid (1:3) has been reported. Nieminen, T. E. A.; Hase, T. A. Tetrahedron Lett. 1987, 28, 4725.
13. 7 Evidently, in this reaction also 2 equiv of the reagent is not necessary.
14. 13C NMR. The MTPA ester of this alcohol was prepared and analyzed using a gas chromatograph fitted with a SPB-5 capillary column, which showed an ee of 95%.
15. 14. Boting, N. P. Chem. Soc. Rev. 1995, 24, 401.
16. 15. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. Organic Syntheses via Boranes Wiley-Interscience: New York, 1975; Chapter 9.