DOI: 10.1002/anie.200700988. Organocatalytic Enantioselective [3+2] Cycloaddition of Azomethine Ylides and α,β‐Unsaturated Aldehydes

Organocatalytic Enantioselective [3+2] Cycloaddition of Azomethine Ylides and α,β‐Unsaturated Aldehydes

10.1002/anie.200700988

Crossref journal-article

Wiley

Angewandte Chemie International Edition (311)

Bibliography

Vicario, J. L., Reboredo, S., BadÃa, D., & Carrillo, L. (2007). Organocatalytic Enantioselective [3+2] Cycloaddition of Azomethine Ylides and Î±,Î²âUnsaturated Aldehydes. Angewandte Chemie International Edition, 46(27), 5168â5170. Portico.

Authors 4

Jose L. Vicario (first)
Silvia Reboredo (additional)
Dolores Badía (additional)
Luisa Carrillo (additional)

References 44 Referenced 226

For selected recent reviews on asymmetric organocatalysis see:
10.1002/ange.200603129
10.1002/anie.200603129
10.1002/ange.200600529
10.1002/anie.200600529
10.1039/b415217b
10.1002/ange.200400650
10.1002/anie.200400650
10.1002/3527604677
10.1021/ja054008q
10.1021/jo060339p
10.1021/ol050590b
10.1021/ol060621i
For reviews see:
10.1016/j.tet.2007.01.009
10.1021/cr040004c
10.1021/cr970324e
10.1021/cr050011g
For reviews see:
10.1002/ange.200501074
10.1002/anie.200501074
10.1016/j.tetasy.2005.05.020
10.1021/ja067346f
10.1021/ol061521f
{'key': 'e_1_2_2_22_2', 'first-page': '543', 'author': 'Bonini B. F.', 'year': '2006', 'journal-title': 'Synlett'} / Synlett by Bonini B. F. (2006)
10.1002/ange.200503672
10.1002/anie.200503672
{'key': 'e_1_2_2_24_2', 'first-page': '1431', 'author': 'Stohler R.', 'year': '2005', 'journal-title': 'Synthesis'} / Synthesis by Stohler R. (2005)
10.1021/ol0516925
10.1021/ja0552186
10.1021/ol0514653
For the first reported organocatalytic asymmetric [3+2] cycloaddition see:
10.1021/ja005517p
10.1016/j.tetlet.2006.11.029
10.1002/adsc.200606102
10.1002/ejoc.200300172
10.1039/cs9871600089
10.1016/S0040-4020(01)80037-5
In a preliminary screening we found that the reaction proceeded more efficiently in polar solvents most probably as a result of their ability to stabilize the 1 3‐dipole formed upon 1 2‐prototropy.
We also tested the following acid cocatalysts: trifluoroacetic acid (13 % yield) para‐toluenesulfonic acid (31 % yield) diphenylacetic acid (60 % yield) acetic acid (65 % yield).
WhenL‐proline (3) or (S)‐α α‐diphenylprolinol (8) were used in an attempted reaction between methyl benzylideneaminoacetate and crotonaldehyde in THF or DMF we did not observe the formation of a cycloaddition product.
10.1021/ja036558z
10.1039/b600647g

Dates

Type	When
Created	18 years, 3 months ago (May 30, 2007, 4:47 a.m.)
Deposited	1 year, 10 months ago (Oct. 16, 2023, 5:18 p.m.)
Indexed	1 year ago (Aug. 6, 2024, 5:57 a.m.)
Issued	18 years, 2 months ago (June 22, 2007)
Published	18 years, 2 months ago (June 22, 2007)
Published Online	18 years, 2 months ago (June 22, 2007)
Published Print	18 years, 1 month ago (July 2, 2007)

Funders 0

None

BibTeX

@article{Vicario_2007, title={Organocatalytic Enantioselective [3+2] Cycloaddition of Azomethine Ylides and α,β‐Unsaturated Aldehydes}, volume={46}, ISSN={1521-3773}, url={http://dx.doi.org/10.1002/anie.200700988}, DOI={10.1002/anie.200700988}, number={27}, journal={Angewandte Chemie International Edition}, publisher={Wiley}, author={Vicario, Jose L. and Reboredo, Silvia and Badía, Dolores and Carrillo, Luisa}, year={2007}, month=jun, pages={5168–5170} }

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