Intermolecular Michael reactions: A computational investigation

Organic Letters

Volumn 12, Issue 22, 2010, Pages 5124-5127

  Kwan, Eugene E ^a   Evans, David A ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; LITHIUM; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

CATIONS; LITHIUM; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 78449282658     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102017v     Document Type: Article

References (16)

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2. Michael, A. Am. J. Chem. 1887, 9, 112-114
3. Perlmutter, P. Conjugate Additions in Organic Synthesis; Tetrahedron Organic Chemistry Series; Pergamon Press: Oxford, 1992; Vol. 9.
4. Oare, D. A.; Heathcock, C. H. Stereochemistry of the Base-Promoted Michael Addition Reaction. In Topics in Stereochemistry; Eliel, E. L.; Wilen, S. H., Eds.; Wiley: New York, 1989; Vol. 19, pp 227 - 408.
5. Rosi, M.; Sgamellotti, A.; Floriani, C. J. Mol. Struct. 1997, 431, 33-46
6. Houk, R. J. T.; Anslyn, E. V.; Stanton, J. F. Org. Lett. 2006, 8, 3461-3463
7. Doubly solvated structures were the overall minimum (triply solvated structures, while enthalpically favored are entropically disfavored. Zuend, S. J.; Ramirez, A.; Lobkovsky, E.; Collum, D. B. J. Am. Chem. Soc. 2006, 128, 6939-6948
8. In contrast to the behavaior of lithioimines (ref 6), serial solvation studies indicated that the triply solvated form of lithioacetone is the overall minimum.
9. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157-167
10. The M05-2X functional has been found to perform well for conjugate additions. Rokob, T. A.; Hamza, A.; Pápai, I. Org. Lett. 2007, 9, 4279-482
11. Frequency analysis confirmed that ground states were true local minima and that transition states had exactly one negative frequency. Single-point energies at M05-2X/6-311+g(d,p)//M05-2X/6-31g(d) gave identical trends (see the Supporting Information).
12. Bernardi, A.; Capelli, A. M.; Comotti, A.; Gennari, C.; Scolastico, C. Tetrahedron Lett. 1991, 32, 823-826
13. Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029-7034
14. Heathcock, C. H.; Oare, D. A. J. Org. Chem. 1985, 50, 3022-3024
15. See the Supporting Information for full details.
16. As judged by trapping as the silyl enol ether: Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868-2877