The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
Tandem Oxidation of Allylic and Benzylic Alcohols to Esters Catalyzed by N-Heterocyclic Carbenes
Abstract
N-heterocyclic carbenes catalyze the oxidation of allylic, propargylic, and benzylic alcohols to esters with manganese(IV) oxide in excellent yields. A variety of ester derivatives can be synthesized, including protected carboxylates. This one-pot tandem oxidation represents the first organocatalytic oxidation of alcohols to esters. Saturated esters can also be accessed from aldehydes using this method. Through the utilization of a chiral catalyst, the acyl-heteroazolium intermediate becomes a chiral acylating agent, which can desymmetrize meso-1,2-diols. [reaction: see text].
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Citations
Cites
Green, Catalytic Oxidations of Alcohols
Sheldon, R. A., Arends, I. W. C. E., ten Brink, G.-J., & Dijksman, A. (2002) · Accounts of Chemical Research · doi:10.1021/ar010075n · Cited by 1,171
Efficient Transesterification/Acylation Reactions Mediated by N-Heterocyclic Carbene Catalysts
Grasa, G. A., Güveli, T., Singh, R., & Nolan, S. P. (2003) · The Journal of Organic Chemistry · doi:10.1021/jo0267551 · Cited by 236
Mirzaei, Y., Twamley, B., & Shreeve, J. M. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo026350g · Cited by 130
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
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
Self-citationCatalysis 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
Zhukhovitskiy, A. V., MacLeod, M. J., & Johnson, J. A. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00220 · Cited by 363
Chen, X., Liu, Q., Chauhan, P., & Enders, D. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201709684 · Cited by 293
Metadata
- Authors
- Maki, B. E., Chan, A., Phillips, E. M., & Scheidt, K. A.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-12-20
- Volume
- 9
- Issue
- 2
- Pages
- 371-374
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2039671444
- Cited by
- 288
- References
- 3
- FWCI
- 6.18
- Type
- journal article
- Language
- en
- Open access
- closed
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