Combining meyer-schuster rearrangement with aldol and mannich reactions: Theoretical study of the intermediate interception strategy

Journal of the American Chemical Society

Volumn 134, Issue 46, 2012, Pages 19159-19169

  Kalek, Marcin ^a   Himo, Fahmi ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,3-SHIFT; ALLENYL; BOND METATHESIS; C-C BOND FORMATION; CATALYTIC CYCLES; ENERGY PROFILE; ENOLATE INTERMEDIATES; ENOLATES; ISOMERIZATION PATHWAYS; MANNICH REACTIONS; MEYER-SCHUSTER REARRANGEMENT; THEORETICAL STUDY;

ALDEHYDES; CHEMICAL BONDS; DENSITY FUNCTIONAL THEORY; KETONES; OLEFINS; STEREOCHEMISTRY; VANADIUM;

REACTION INTERMEDIATES;

ALLENYL ENOLATE; CARBON; ENOLATE; MANNICH BASE; TRIPHENYLSILOXY; UNCLASSIFIED DRUG; VANADIC ACID; VANADIUM;

ALDOL REACTION; ALLYLIC REARRANGEMENT; ARTICLE; CALCULATION; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENERGY; ISOMERIZATION; MEYER SCHUSTER REARRANGEMENT; STEREOCHEMISTRY; THEORETICAL STUDY; TRANSESTERIFICATION;

EID: 84869426982     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja307892c     Document Type: Article

References (21)

1. Trost, B. M. Angew. Chem., Int. Ed. 1995, 34, 259-281
2. Trost, B. M.; Oi, S. J. Am. Chem. Soc. 2001, 123, 1230-1231
3. Trost, B. M.; Chung, C. K. J. Am. Chem. Soc. 2006, 128, 10358-10359
4. Pauling, H.; Andrews, D. A.; Hindley, N. C. Helv. Chim. Acta 1976, 59, 1233-1243
5. Engel, D. A.; Dudley, G. B. Org. Biomol. Chem. 2009, 7, 4149-4158
6. Bartoszewicz, A.; Livendahl, M.; Marítn-Matute, B. Chem. Eur. J. 2008, 14, 10547-10550
7. Shintani, R.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 4082-4085
8. Lin, S.; Zhao, G.-L.; Deiana, L.; Sun, J.; Zhang, Q.; Leijonmarck, H.; Córdova, A. Chem. Eur. J. 2010, 16, 13930-13934
9. Frisch, M. J.; Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
10. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
11. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283
12. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799
13. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995-2001
14. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669-681
15. Ernan, M. B.; Aul'chenko, I. S.; Kheifits, L. A.; Dulova, V. G.; Novikov, J. N.; Vol'pin, M. E. Tetrahedron Lett. 1976, 17, 2981-2984
16. Crans, D. C.; Smee, J. J.; Gaidamauskas, E.; Yang, L. Chem. Rev. 2004, 104, 849-902
17. Niu, S.; Hall, M. B. Chem. Rev. 2000, 100, 353-406
18. Olson, G. L.; Morgan, K. D.; Saucy, G. Synthesis 1976, 25-26
19. Branchadell, V.; Crevisy, C.; Grée, R. Chem. Eur. J. 2004, 10, 5795-5803
20. Chabardes, P.; Kuntz, E.; Varagnat, J. Tetrahedron 1977, 33, 1775-1783
21. Trost, B. M.; Jonasson, C.; Wuchrer, M. J. Am. Chem. Soc. 2001, 123, 12736-12737