Design, synthesis and applications of a ketone reduction catalyst containing a phosphinamide combined with a dioxaborolidine unit

Tetrahedron Asymmetry

Volumn 7, Issue 11, 1996, Pages 3071-3074

  Gamble, Mark P ^a   Studley, John R ^b   Wills, Martin ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b UNIVERSITY OF BATH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; BENZYL ALCOHOL DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030575799     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00400-4     Document Type: Article

References (15)

1. 1) (a) B. Burns, J. R. Studley and M. Wills, Tetrahedron Lett., 1993, 34, 7105.
2. (b) B. Burns, N. P. King, J. R. Studley, H. Tye and M. Wills, Tetrahedron: Asymmetry, 1994, 5, 801.
3. 2) M. P. Gamble, J. R. Studley and M. Wills, Tetrahedron Lett., 1996, 37, 2853.
4. 3) O. Chiodi, F. Fotiadu, M. Sylvestre and G. Buono, Tetrahedron Lett., 1996, 37, 39.
5. 4) R. Hulst, H. Heres, N. C. M. W. Peper and R. M. Kellogg, Tetrahedron: Asymmetry, 1996, 7, 1373.
6. 5) (a) K. Otsuka, K. Ito and T. Katsuki, Synlett., 1995, 429.
7. (b) R. Berenguer, J. Garcia, M. Gonzalez and J. Vilarrasa, Tetrahedron: Asymmetry, 1993, 4, 13.
8. 6) (a) M. Canas, M. Poch, X. Verdaguer, A. Moyano, M. A. Pericas and A. Riera, Tetrahedron Lett., 1991, 32, 6931.
9. (b) M. Meguro, N. Asao and Y. Yamamoto, J. Chem. Soc., Perkin Trans. 1. 1994, 2597.
10. (c) M. Chini, P. Crotti and F. Macchia, Tetrahedron Lett., 1990, 31, 4661.
11. 10 approach to the synthesis of 3a. It is noteworthy that this reaction, mediated by AD-mix-α or in the case of the omission of a chiral ligand, gave exactly the same mixture of products in each case, which suggests diastereoisomeric control entirely by the amine side chain. (formula presented)
12. 8) J. M. Brunel, M. Maffei and G. Buono, Tetrahedron: Asymmetry, 1993, 4, 2255.
13. 9) (a) G. B. Stone, Tetrahedron: Asymmetry, 1994, 5, 465.
14. (b) A. W. Douglas, D. M. Tschaen, R. A. Reamer and Y.-J. Shi, Tetrahedron: Asymmetry, 1996, 7, 1303, and references therein.
15. 10) (a) P. J. Walsh, Y. L. Bennani and K. B. Sharpless, Tetrahedron Lett., 1993, 34, 5545.