Noninnocent role of N -methyl pyrrolidinone in thiazolidinethione-promoted asymmetric aldol reactions

Organic Letters

Volumn 14, Issue 22, 2012, Pages 5752-5755

  Sreenithya, A ^a   Sunoj, Raghavan B ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84869175016     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302761n     Document Type: Article

References (26)

1. Palomo, C.; Oiarbide, M.; García, J. M. Chem. Soc. Rev. 2004, 33, 65
2. Brodmann, T.; Lorenz, M.; Schäckel, R.; Simsek, S.; Kalesse, M. Synlett 2009, 174
3. Geary, L. M.; Hultin, P. G. Tetrahedron: Asymmetry 2009, 20, 131
4. Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894
5. Crimmins, M. T.; Chaudhary, K. Org. Lett. 2000, 2, 775
6. Crimmins, M. T.; She, J. Synlett 2004, 8, 1371
7. Liu, J.; Zhang, L.; He, J.; He, L.; Ma, B.; Pan, X.; She, X. Tetrahedron: Asymmetry 2008, 19, 906
8. Trost, B. M.; OBoyle, B. M.; Hund, D. J. Am. Chem. Soc. 2009, 131, 15061
9. Burnett, C. M.; Williams, R. M. Tetrahedron Lett. 2009, 50, 5449
10. Zou, Y.; Wu, Y. Angew. Chem., Int. Ed. 2012, 51, 4968
11. Patel, J.; Clave, G.; Renard, P.-Y.; Franck, X. Angew. Chem., Int. Ed. 2008, 47, 1
12. The reaction holds promise in providing easier access to a syn α-amino-β-hydroxy acid or acid derivatives. Such structural elements are known to be important in several biologically active compounds.
13. Shinisha, C. B.; Sunoj, R. B. J. Am. Chem. Soc. 2010, 132, 12319
14. Shinisha, C. B.; Sunoj, R. B. Org. Lett. 2010, 12, 2868
15. Shinisha, C. B.; Sunoj, R. B. Org. Lett. 2009, 11, 3242
16. Sharma, A. K.; Sunoj, R. B. Angew. Chem., Int. Ed. 2010, 49, 6373
17. Rajeev, R.; Sunoj, R. B. J. Org. Chem. 2012, 77, 2474
18. Jindal, G.; Sunoj, R. B. Chem.-Eur. J. 2012, 18, 7045
19. Reddi, Y.; Sunoj, R. B. Org. Lett. 2012, 14, 2810
20. All calculations were performed using Gaussian09. Frisch, M. J. Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2004. See Supporting Information (SI) for full citation.
21. Full details of computational methods, including at the mPW1K level of theory, are provided in the SI. The gas-phase free energies exhibit identical trends. See SI (Tables S1-S5).
22. The asymmetric carbon in the chiral auxiliary is in the R configuration.
23. -1, both of these configurations are considered in this study.
24. Details of the activation-strain analysis (wherein the activation barrier is partitioned into interaction energy between the reacting partners and distortion energy within each partner at the TS as a result of the bond formation) are provided in Tables S6 and S7 in the SI.
25. van Zeist, W. J.; Bickelhaupt, F. M. Org. Biomol. Chem. 2010, 8, 3118
26. Legault, C. Y.; Garcia, Y.; Merlic, C. A.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 12664