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N-Heterocyclic Carbene-Catalyzed Generation of Homoenolates: γ-Butyrolactones by Direct Annulations of Enals and Aldehydes
Abstract
N-Heterocyclic carbenes, prepared in situ from diarylimidazolium salts, serve as highly effective catalysts for the generation of reactive homoenolates from alpha,beta-unsaturated aldehydes. The catalyst-bound homoenolate reacts with electrophilic aldehydes leading, via the key intermediacy of an activated carboxylate, to gamma-butyrolactones in good yields and stereoselectivities. Importantly, this process demonstrates an unprecedented reaction mode for the generation of nucleophilic carbanions with a multifunctional organocatalyst under exceptionally mild and convenient reaction conditions.
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Cited by
Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes
Flanigan, D. M., Romanov-Michailidis, F., White, N. A., & Rovis, T. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00060 · Cited by 2,045
Organocatalytic Ring-Opening Polymerization
Kamber, N. E., Jeong, W., Waymouth, R. M., Pratt, R. C., Lohmeijer, B. G. G., & Hedrick, J. L. (2007) · Chemical Reviews · doi:10.1021/cr068415b · Cited by 1,489
A Continuum of Progress: Applications of N‐Hetereocyclic Carbene Catalysis in Total Synthesis
Izquierdo, J., Hutson, G. E., Cohen, D. T., & Scheidt, K. A. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201203704 · Cited by 537
Catalysis with N‐Heterocyclic Carbenes under Oxidative Conditions
De Sarkar, S., Biswas, A., Samanta, R. C., & Studer, A. (2013) · Chemistry – A European Journal · doi:10.1002/chem.201203707 · Cited by 503
N‐heterocyclische Carbene als Organokatalysatoren
Marion, N., Díez‐González, S., & Nolan, S. P. (2007) · Angewandte Chemie · doi:10.1002/ange.200603380 · Cited by 428
Chen, X.-Y., Gao, Z.-H., & Ye, S. (2020) · Accounts of Chemical Research · doi:10.1021/acs.accounts.9b00635 · Cited by 386
Zhou, H., Zhang, W.-Z., Liu, C.-H., Qu, J.-P., & Lu, X.-B. (2008) · The Journal of Organic Chemistry · doi:10.1021/jo801457r · Cited by 364
Zhukhovitskiy, A. V., MacLeod, M. J., & Johnson, J. A. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00220 · Cited by 363
A Dual Lewis Base Activation Strategy for Enantioselective Carbene-Catalyzed Annulations
Izquierdo, J., Orue, A., & Scheidt, K. A. (2013) · Journal of the American Chemical Society · doi:10.1021/ja405833m · Cited by 332
Chen, X., Liu, Q., Chauhan, P., & Enders, D. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201709684 · Cited by 293
Enantioselective Chemo‐ and Biocatalysis: Partners in Retrosynthesis
Hönig, M., Sondermann, P., Turner, N. J., & Carreira, E. M. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201612462 · Cited by 284
Metadata
- Authors
- Sohn, S. S., Rosen, E. L., & Bode, J. W.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-10-13
- Volume
- 126
- Issue
- 44
- Pages
- 14370-14371
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2034837626
- Cited by
- 704
- References
- 0
- FWCI
- 12.29
- Type
- journal article
- Language
- en
- Open access
- closed
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