Aminoborohydrides. 14. Lithium aminoborohydrides in the selective reduction or amination of alkyl methanesulfonate esters

Organic Letters

Volumn 3, Issue 24, 2001, Pages 3915-3918

  Thomas, Shannon ^a   Huynh, Tai ^a   Enriquez Rios, Vanessa ^a   Singaram, Bakthan ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0008923746     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0167659     Document Type: Article

References (14)

1. Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85.
2. March, J. Advanced Organic Chemistry, 4th ed; Wiley and Sons: New York, 1992; pp 441-442.
3. Gaylord, N. G. Reduction with Complex Metal Hydrides; Interscience Publishers: New York, 1956; pp 855-875.
4. (a) Krishnamurthy, S.; Brown, H. C. J. Org. Chem. 1976, 41, 3064. (b) Super-Hydride is a registered trademark of Sigma-Aldrich Chemical Co.
5. Fisher, G. B.; Harrison, J.; Fuller, J. C.; Goralski, C. T.; Singaram, B. Tetrahedron Lett. 1992, 33, 4533.
6. Collins, C. J.; Lanz, M.; Goralski, C. T.; Singaram, B. J. Org. Chem. 1999, 64, 2574.
7. Thomas, S.; Collins, C. J.; Cuzens, J. R.; Spiciarich, D.; Goralski, C. T.; Singaram, B. J. Org. Chem. 2001, 66, 1999.
8. 11B NMR spectra.
9. Harrison, J.; Alvarez, S. G.; Godjoian, G.; Singaram, B. J. Org. Chem. 1994, 59, 7193.
10. Brown, H. C.; Singaram, B.; Singaram, S. J. Organomet. Chem. 1982, 239, 43.
11. Brown, H. C.; Kim, S. C.; Krishnamurthy, S. J. Org. Chem. 1980, 45, 1.
12. Holder, R. W.; Mattuno, M. G. J. Org. Chem. 1977, 42, 2166.
13. 3BH substantially decreases the amount of pyrophoric material for a given reduction.
14. 2 is added dropwise. See refs 5, 6, or 7 for a more detailed description of LAB handling and quenching. (CAUTION!, if quenched with 3 M HCl, hydrogen evolution!) After 15 min, a 0.1 mL aliquot is removed from the reaction mixture and placed in 1 mL of pentane (LAB and amine-boranes are insoluble in pentane). The sample is filtered through a syringe filter and analyzed by GC. Yields reported are GC yields, utilizing an internal standard and corrected for detector response.