Highly enantioselective hydrogenation of cyclic enol acetates catalyzed by a Rh - PennPhos complex

Angewandte Chemie - International Edition

Volumn 38, Issue 4, 1999, Pages 516-518

  Jiang, Qiongzhong ^a   Xiao, Dengming ^a   Zhang, Zhaoguo ^a   Cao, Ping ^a   Zhang, Xumu ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

Alcohols; Asymmetric catalysis; Enols; Hydrogenations; Rhodium

Indexed keywords

BISPHOSPHONIC ACID DERIVATIVE; LIGAND; RHODIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHELATION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; HYDROGENATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033557426     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19990215)38:4<516::aid-anie516>3.0.co;2-b     Document Type: Article

References (20)

1. a) Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993;
2. b) R. A. Sheldon, Chirotechnology, Marcel Dekker, New York, 1993;
3. c) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994;
4. d) R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345;
5. e) M. J. Burk, M. F. Gross, G. P. Harper, C. S. Kalberg, J. R. Lee, J. P. Martinez, Pure Appl. Chem. 1996, 65, 37.
6. For the synthesis of enol esters, see R. C. Larock, Comprehensive Organic Transformations, VCH, New York, 1989, p. 743.
7. For selected examples of asymmetric hydrogenations of enol acetates, see a) K. E. Koening, G. L. Bachman, B. D. Vineyard, J. Org. Chem. 1980, 45, 2362;
8. b) R. E. Merrill, ChemTech 1981, 118;
9. c) T. Hayashi, K. Kanehira, M. Kumada, Tetrahedron Lett. 1981, 22, 4417;
10. d) J. M. Brown, B. A. Murrer, J. Chem. Soc. Perkin Trans. 2 1982, 489;
11. e) K. E. Koening in Asymmetric Synthesis, Vol. 5 (Ed.: J. D. Morrison), Academic Press, Orlando, 1985, p. 71;
12. f) M. J. Burk, J. Am. Chem. Soc. 1991, 113, 8518;
13. g) T. Ohta, T. Miyake, N. Seido, H. Kumobayashi, S. Akutagawa, H. Takaya, Tetrahedron Lett. 1992, 33, 635;
14. h) Y. Crameri, R. Schmid, T. Siegfried (Hoffmann-La Roche AG), EP-B 0691325 A1, 1996 [Chem. Abstr. 1996, 124, 260450x];
15. M. J. Burk, C. S. Kalberg, A. Pizzano, J. Am. Chem. Soc. 1998, 120, 4345;
16. j) N. W. Boaz, Tetrahedron Lett. 1998, 39, 5505.
17. a) G. Zhu, Z. Chen, Q. Jiang, D. Xiao, P. Cao, X. Zhang, J. Am. Chem. Soc. 1997, 119, 3836;
18. b) Z. Chen, Q. Jiang, G. Zhu, D. Xiao, P. Cao, C. Guo, X. Zhang, J. Org. Chem. 1997, 62, 4521;
19. c) Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. 1998, 110, 1203;
20. Angew. Chem. Int. Ed. 1998, 57, 1100.