Co-reporter:Feng Wang, Shengle Lu, Bo Chen, Yali Zhou, Ying Yang, and Guisheng Deng
Organic Letters 2016 Volume 18(Issue 24) pp:6248-6251
Publication Date(Web):December 5, 2016
DOI:10.1021/acs.orglett.6b02973
The AgSbF6-catalyzed cyclization of 2-diazo-3,5-dioxo-6-ynoates (ynones, ynamide) in alcoholic solvents affords γ-pyrones, whereas the AgOAc-catalyzed cyclization in 1,2-dichloroethane (DCE) produces 3(2H)-furanones. The cyclization reactions proceeded cleanly under mild reaction conditions, and the desired γ-pyrones or 3(2H)-furanones were obtained in excellent yield. It was observed for the first time that both the catalyst and solvent play key roles in the selective formation. This unique method for the reversal of regioselectivity proved to be highly efficient except for substrates with aliphatic and Me3Si groups at the triple bond position.
Co-reporter:Guisheng Deng, Feng Wang, Shengle Lu, and Bo Cheng
Organic Letters 2015 Volume 17(Issue 19) pp:4651-4653
Publication Date(Web):September 15, 2015
DOI:10.1021/acs.orglett.5b02369
The construct of the core of pyrano[3,2-c]pyrazol-7(1H)-one derivatives is realized. The key step includes a tandem cyclization, namely, a metal-free cascade 6-π electrocyclic ring closure-Michael reaction of 2-diazo-3,5-dioxo-6-ynoates (ynones). The cascade reaction cleanly generated the desired products in excellent yields under mild conditions.
Co-reporter:Guisheng Deng, Jing Luo
Tetrahedron 2013 69(29) pp: 5937-5944
Publication Date(Web):
DOI:10.1016/j.tet.2013.04.122
Co-reporter:Gui Sheng Deng, Teng Fei Sun
Chinese Chemical Letters 2012 Volume 23(Issue 10) pp:1115-1118
Publication Date(Web):October 2012
DOI:10.1016/j.cclet.2012.07.017
A novel reaction of trimethylsilylated arylacetylenes with sulfonyl chlorides was performed in the presence of silver nitrate or triflate. Conjugated vinyl sulfones as dramatic products were obtained in moderate yields and with Z-selectivity. A free radical mechanism has been proposed to account for the formation of the products.
Co-reporter:Gui Sheng Deng, Jing Yuan Zou, Teng Fei Sun
Chinese Chemical Letters 2011 Volume 22(Issue 5) pp:511-514
Publication Date(Web):May 2011
DOI:10.1016/j.cclet.2010.11.019
A new method for preparation of N-tosylimines by InCl3-mediated condensation of aldehydes with p-toluenesulfonamide in refluxing benzene is reported. The procedure is lauded by its simplicity, mild reaction conditions, excellent yields and adaptability to electron deficient and electron rich aromatic, and α,β-unsaturated aldehydes.