The DOI matches its Crossref record; 2 of the 2 references it cites were found in a registry or an index.
Dienamine Catalysis: Organocatalytic Asymmetric γ-Amination of α,β-Unsaturated Aldehydes
Abstract
A new concept in organocatalysis is presented, the direct asymmetric gamma-functionalization of alpha,beta-unsaturated aldehydes. We disclose that secondary amines can invert the usual reactivity of alpha,beta-unsaturated aldehydes, enabling a direct gamma-amination of the carbonyl compound using azodicarboxylates as the electrophilic nitrogen-source. The scope of the reaction is demonstrated for the enantioselective gamma-amination of different alpha,beta-unsaturated aldehydes, giving the products in moderate to good yields and with high enantioselectivities up to 93% ee. Experimental investigations and DFT calculations indicate that the reaction might proceed as a hetero-Diels-Alder cycloaddition reaction. Such a mechanism can explain the "unexpected" stereochemical outcome of the reaction.
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Cites
Lee, C., Yang, W., & Parr, R. G. (1988) · Physical Review B · doi:10.1103/physrevb.37.785 · Cited by 100,874
A new mixing of Hartree–Fock and local density-functional theories
Becke, A. D. (1993) · The Journal of Chemical Physics · doi:10.1063/1.464304 · Cited by 16,515
Cited by
Asymmetric Aminocatalysis—Gold Rush in Organic Chemistry
Melchiorre, P., Marigo, M., Carlone, A., & Bartoli, G. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200705523 · Cited by 1,256
Self-citationLiu, Y., Nappi, M., Arceo, E., Vera, S., & Melchiorre, P. (2011) · Journal of the American Chemical Society · doi:10.1021/ja206517s · Cited by 398
Metadata
- Authors
- Bertelsen, S., Marigo, M., Brandes, S., Dinér, P., & Jørgensen, K. A.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-09-09
- Volume
- 128
- Issue
- 39
- Pages
- 12973-12980
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2031068701
- Cited by
- 404
- References
- 2
- FWCI
- 14.76
- Type
- journal article
- Language
- en
- Open access
- closed
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