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Li M, Kong XJ, Wen LR. Yb(OTf)3-Mediated Access to Furans from β-Ketothioamides via Eschenmoser Sulfide Contraction Reaction. J Org Chem. 2015;80(24):11999-2005doi: 10.1021/acs.joc.5b01924.
Li, M., Kong, X. J., & Wen, L. R. (2015). Yb(OTf)3-Mediated Access to Furans from β-Ketothioamides via Eschenmoser Sulfide Contraction Reaction. The Journal of organic chemistry, 80(24), 11999-2005. https://doi.org/10.1021/acs.joc.5b01924
Li, Ming, et al. "Yb(OTf)3-Mediated Access to Furans from β-Ketothioamides via Eschenmoser Sulfide Contraction Reaction." The Journal of organic chemistry vol. 80,24 (2015): 11999-2005. doi: https://doi.org/10.1021/acs.joc.5b01924
Li M, Kong XJ, Wen LR. Yb(OTf)3-Mediated Access to Furans from β-Ketothioamides via Eschenmoser Sulfide Contraction Reaction. J Org Chem. 2015 Dec 18;80(24):11999-2005. doi: 10.1021/acs.joc.5b01924. Epub 2015 Nov 18. PMID: 26551164.
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J Org Chem. 2015 Dec 18;80(24):11999-2005. doi: 10.1021/acs.joc.5b01924. Epub 2015 Nov 18.

Yb(OTf)3-Mediated Access to Furans from β-Ketothioamides via Eschenmoser Sulfide Contraction Reaction.

The Journal of organic chemistry

Ming Li, Xiang-Jing Kong, Li-Rong Wen

Affiliations

  1. State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology , Qingdao 266042, P. R. China.

PMID: 26551164 DOI: 10.1021/acs.joc.5b01924

Abstract

A mild and straightforward synthetic protocol for construction of a furan skeleton promoted by Yb(OTf)3 from β-ketothioamides and arylglyoxals has been developed at room temperature. Importantly, this protocol involves a tandem sequence that includes aldol condensation, N-cyclization, ring opening, O-cyclization, S-cyclization, and Eschenmoser sulfide contraction.

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