Highly efficient asymmetric hydrogenation of 2-methylenesuccinamic acid using a Rh-DuPHOS catalyst

Organic Process Research and Development

Volumn 7, Issue 3, 2003, Pages 407-411

  Cobley, Christopher J ^a   Lennon, Ian C ^a   Praquin, Céline ^a   Zanotti Gerosa, Antonio ^a   Appell, Robert B ^a   Goralski, Christian T ^a   Sutterer, Angela C ^a  

^a DOW CHEMICAL COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLENESUCCINAMIC ACID; RHODIUM COMPLEX; SUCCINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL PARAMETERS; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGENATION; REACTION OPTIMIZATION;

EID: 0037708561     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0256183     Document Type: Article

References (21)

1. For an example of the use of -2-methylsuccinamic acid, see: (a) Ikeura, Y.; Doi, T.; Fujishima, A.; Natsugari, H. Chem. Commun. 1998, 2141-2142. (b) Natsugari, H.; Ikeura, Y.; Kamo, I.; Ishimaru, T.; Ishichi, Y.; Fujishima, A.; Tanaka, T.; Kasahara, F.; Kawada, M.; Natsugari, H. J. Med. Chem. 1999, 42, 3982-3993.
2. For an example of the use of -2-methylsuccinamic acid, see: (a) Ikeura, Y.; Doi, T.; Fujishima, A.; Natsugari, H. Chem. Commun. 1998, 2141-2142. (b) Natsugari, H.; Ikeura, Y.; Kamo, I.; Ishimaru, T.; Ishichi, Y.; Fujishima, A.; Tanaka, T.; Kasahara, F.; Kawada, M.; Natsugari, H. J. Med. Chem. 1999, 42, 3982-3993.
3. For an example of the use of -2-methylsuccinamic acid, see: Fuji, T.; Ogawa, N. Tetrahedron Lett. 1972, 13, 3075-3078.
4. (a) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Ed.; Wiley-Interscience: New York, 1994.
5. (b) Comprehensive Asymmetric Catalysis; Jacobsen. E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 1.
6. (c) Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
7. For industrial examples of asymmetric hydrogenation, see: Blaser, H. U.; Spindler, F.; Studer, M. Appl. Catal. A: Gen. 2001, 221, 119-143.
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9. 5-Fc = 1, 1′-bis(2,5-dialkylphospholano)ferrocene
10. COD = 1,5-cyclooctadiene
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16. 5 the major product for this reaction was assigned as (R)-2-methylsuccinamic acid. This corresponds to the first eluting enantiomer in the GC method used.
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19. See draft guidelines from the European Agency for the Evaluation of Medicinal Products, 27 June 2002, http://www.emea.eu.int/pdfs/human/swp/444600en.pdf
20. 2, dd, J = 7.3 and 15.3), and 1.10 (3H, CH3, d, J = 7.0)
21. Adams, R., Fles, D. J. Am. Chem. Soc. 1959, 81, 4946-4951.