Protonation-assisted conjugate addition of axially chiral enolates: Asymmetric synthesis of multisubstituted β-lactams from α-amino acids

Chemistry - A European Journal

Volumn 18, Issue 48, 2012, Pages 15330-15336

  Yoshimura, Tomoyuki ^a   Takuwa, Masatoshi ^a   Tomohara, Keisuke ^a   Uyama, Makoto ^a   Hayashi, Kazuhiro ^a   Yang, Pan ^a   Hyakutake, Ryuichi ^a   Sasamori, Takahiro ^a   Tokitoh, Norihiro ^a   Kawabata, Takeo ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

lactams; amino acids; axial chirality; conjugate addition; protonation

Indexed keywords

ASYMMETRIC SYNTHESIS; AXIAL CHIRALITY; CONJUGATE ADDITION; ENANTIOSELECTIVE; ENOLATES; HIGHLY STRAINED; INTRAMOLECULAR CONJUGATE ADDITION; LOW CONCENTRATIONS; METAL CARBONATES; P-METHOXYBENZYL; PROTIC SOLVENTS; REACTION MEDIA; SIDE REACTIONS; WEAK BASE;

AMINO ACIDS; CARBON; CYCLIZATION; ENANTIOSELECTIVITY; OLEFINS; PROTONATION;

AMIDES;

AMINO ACID; BETA LACTAM; CARBOXYLIC ACID; SOLVENT;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HYDROGENATION; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; BETA-LACTAMS; CARBOXYLIC ACIDS; CATALYSIS; CYCLIZATION; HYDROGENATION; MOLECULAR STRUCTURE; SOLVENTS; STEREOISOMERISM;

EID: 84869450468     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201339     Document Type: Article

References (27)

1. T. Kawabata, S. Majumdar, K. Tsubaki, D. Monguchi, Org. Biomol. Chem. 2005, 3, 1609-1611.
2. T. Kawabata, K. Fuji, Top. Stereochem. 2003, 23, 175-205
3. H. Zhao, D. C. Hsu, P. R. Carlier, Synthesis 2005, 1-16
4. T. Kawabata, Asymmetric Synthesis and Application of α-Amino Acids, in ACS Symposium Series 1009, 2009, pp. 31-56. For recent examples of asymmetric synthesis based on memory of chirality, see
5. P. R. Carlier, H. Zhao, S. L. MacQuarrie-Hunter, J. C. DeGuzman, D. C. Hsu, J. Am. Chem. Soc. 2006, 128, 15215-15220
6. L. Kolaczkowski, D. M. Barnes, Org. Lett. 2007, 9, 3029-3032
7. M. Branca, D. Gori, R. Guillot, V. Alezra, C. Koulovsky, J. Am. Chem. Soc. 2008, 130, 5864-5865.
8. We highly appreciate Cozzi and Siegel's suggestion on memory of chirality (, F. Cozzi, J. S. Siegel, Org. Biomol. Chem. 2005, 3, 4296-4298). While we completely agree with their definition of stereochemistry, we have used the term "memory of chirality" from the following viewpoint. "Memory of chirality" represents the phenomena in which static chirality (mostly central chirality) is preserved as transient chirality (mostly axial chirality) in the reactive intermediate, and then regenerated as static chirality in the product
9. T. Kawabata, K. Yahiro, K. Fuji, J. Am. Chem. Soc. 1991, 113, 9694-9696).
10. D. Monguchi, S. Majumdar, T. Kawabata, Heterocycles 2006, 68, 2571-2578.
11. G. Gerona-Navarro, M. A. Bonache, R. Hernz, M. T. García- Lõpez, R. González-Muñiz, J. Org. Chem. 2001, 66, 3538-3547
12. M. A. Bonache, G. Gerona-Navarro, M. Martín-Martínez, M. T. García-Lõpez, P. Lõpez, C. Cativiela, R. González-Muñiz, Synlett 2003, 1007-1011
13. M. A. Bonache, G. Gerona-Navarro, C. García-Aparicio, M. Alías, M. Martín-Martínez, M. T. García-Lõpez, P. Lõpez, C. Cativiela, R. González-Muñiz, Tetrahedron: Asymmetry 2003, 14, 2161-2169
14. M. A. Bonache, C. Cativiela, M. T. García-Lõpez, R. González-Muñiz, Tetrahedron Lett. 2006, 47, 5883-5887.
15. An interesting method for the synthesis of β-lactams with contiguous tetra- and trisubstituted carbon centers was recently reported in which the stereochemistry was controlled by the chirality of the intramolecular electrophile. See:, P. Pérez-Faginas, F. O'Reilly, A. O'Byrne, C. García-Aparcio, M. Martín-Martínez, M. J. Pérez de Vaga, M. T. García-Lõpez, R. González-Muñiz, Org. Lett. 2007, 9, 1593-1596.
16. β-Lactam synthesis through irreversible intramolecular conjugate addition of α-lithio amides has been reported, see:, J. Clayden, D. W. Watson, M. Helliwell, M. Chambers, Chem. Commun. 2003, 2582-2583.
17. T. Kawabata, S. Kawakami, D. Majumdar, J. Am. Chem. Soc. 2003, 125, 13012-13013
18. LTMP is a suitable base for the intramolecular alkylation of α-amino acid derivatives with an inversion of configuration through memory of chirality, see:, T. Kawabata, S. Matsuda, S. Kawakami, D. Monguchi, K. Moriyama, J. Am. Chem. Soc. 2006, 128, 15394-15395.
19. F. G. Bordwell, Acc. Chem. Res. 1988, 21, 456-463
20. N. V. Mashchenko, M. G. Matveeva, I. L. Odinets, E. I. Matrosov, E. S. Petrov, M. I. Terekhova, A. K. Matveev, T. A. Mastryukova, M. I. Kabachnik, Zh. Obshch. Khim. 1988, 58, 1973-1979
21. R. P. Bell, The Proton in Chemistry, Cornell University Press, Ithaca, New York 1959.
22. T. Kawabata, K. Moriyama, S. Kawakami, K. Tsubaki, J. Am. Chem. Soc. 2008, 130, 4153-4157.
23. T. Kawabata, H. Suzuki, Y. Nagae, K. Fuji, Angew. Chem. 2000, 112, 2239-2241
24. Angew. Chem. Int. Ed. 2000, 39, 2155-2157, also see refs. [2a,c, 10, 11, 13].
25. Recently, a highly enantioselective cascade rearrangement of enediynes has been reported that proceeds at 80 C through memory of chirality, see:, M. Nechab, D. Campolo, J. Maury, P. Perfetti, N. Vanthuyne, D. Siri, M. P. Bertrand, J. Am. Chem. Soc. 2010, 132, 14742-14744.
26. For a recent example, see:, C. Palomo, J. M. Aizpurua, E. Balentová, A. Jimenez, J. Oyarbide, R. M. Fratile, J. I. Miranda, Org. Lett. 2007, 9, 101-104.
27. B. Alcaide, P. Almendros, C. Aragoncillo, Chem. Rev. 2007, 107, 4437-4492.