Application of MerCO as a chiral catalyst in asymmetric synthesis: Asymmetric borane reduction of ketones

Tetrahedron Asymmetry

Volumn 10, Issue 3, 1999, Pages 405-409

  Yang, Teng Kuei ^a   Lee, Dong Sheng ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; BORANE DERIVATIVE; CAMPHENE; KETONE DERIVATIVE; SOLVENT; THIOL; TOLUENE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; PRIORITY JOURNAL; REDUCTION; SYNTHESIS; TEMPERATURE;

EID: 0033548183     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00504-7     Document Type: Article

References (16)

1. Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763.
2. Midland, M. M. Asymmetric Synthesis, Vol 2, Academic Press: New York, 1983, pp. 45-70, and references cited therein.
3. Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1987, and references cited therein.
4. Bolm, C.; Felder, M. Tetrahedron Lett. 1993, 34, 6041 and 8079.
5. Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551.
6. For sulfur containing chiral catalysts in borane reduction see: (a) Li, X.; Xie, R. Tetrahedron: Asymmetry 1996, 7, 2779. (b) Trentmann, W.; Mehler, T.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2033. (c) Calmes, M.; Escale, F.; Paolini, F. Tetrahedron: Asymmetry 1997, 8, 3691.
7. For sulfur containing chiral catalysts in borane reduction see: (a) Li, X.; Xie, R. Tetrahedron: Asymmetry 1996, 7, 2779. (b) Trentmann, W.; Mehler, T.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2033. (c) Calmes, M.; Escale, F.; Paolini, F. Tetrahedron: Asymmetry 1997, 8, 3691.
8. For sulfur containing chiral catalysts in borane reduction see: (a) Li, X.; Xie, R. Tetrahedron: Asymmetry 1996, 7, 2779. (b) Trentmann, W.; Mehler, T.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2033. (c) Calmes, M.; Escale, F.; Paolini, F. Tetrahedron: Asymmetry 1997, 8, 3691.
9. (a) A preliminary presentation was given by us in the 1st National Symposium for Organic Chemistry, Chengdu, China, 1997, IL 18.
10. (b) Zhou, Y. G.; Hou, X. L.; Dai, L. X. Chin. J. Chem. 1998, 16, 284.
11. (a) Lee, D.-S.; Hung, S.-M.; Lai, M.-C.; Chu, H.-Y.; Yang, T.-K. Org. Prep. Proc. Int. 1993, 25, 673.
12. (b) Yang, T.-K.; et al. J. Org. Chem. 1994, 59, 914.
13. Pinho, P.; Guijarro, D.; Andersson, P. G. Tetrahedron 1998, 54, 7897, and references cited therein.
14. (a) Brunel, J.-M.; Pardigon, O.; Faure, B.; Buono, G. J. Chem. Soc., Chem. Commun. 1992, 287.
15. (b) Private communication with Prof. Dai Li-Xin at Shanghai Institute of Organic Chemistry in China.
16. 2 at specified temperature and stirred for 60 min. The ketone was added slowly over a period of 60 min then stirred at specified temperature for another 30 min. The reaction mixture was quenched with 3N NaOH (aq.) and extracted with ethyl acetate. The organic layer was concentrated in vacuum and passed through a short silica column, then subjected to HPLC analysis.