TY - JOUR
T1 - Copper-Catalyzed Coupling of 2-Siloxy-1-alkenes and Diazocarbonyl Compounds
T2 - Approach to Multisubstituted Furans, Pyrroles, and Thiophenes
AU - Tan, Wei Wen
AU - Yoshikai, Naohiko
N1 - Funding Information:
This work was supported by the Ministry of Education of Singapore and Nanyang Technological University (RG 5/14).
Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/7/1
Y1 - 2016/7/1
N2 - We report herein copper(II)-catalyzed cyclization reactions of silyl enol ethers derived from methyl ketones with α-diazo-β-ketoesters or α-diazoketones to afford 2-siloxy-2,3-dihydrofuran derivatives or 2,3,5-trisubstituted furans, respectively, under mild conditions. The former cyclization products serve as versatile 1,4-diketone surrogates, allowing facile preparation of 2,3,5-trisubstituted furans, pyrroles, and thiophenes.
AB - We report herein copper(II)-catalyzed cyclization reactions of silyl enol ethers derived from methyl ketones with α-diazo-β-ketoesters or α-diazoketones to afford 2-siloxy-2,3-dihydrofuran derivatives or 2,3,5-trisubstituted furans, respectively, under mild conditions. The former cyclization products serve as versatile 1,4-diketone surrogates, allowing facile preparation of 2,3,5-trisubstituted furans, pyrroles, and thiophenes.
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U2 - 10.1021/acs.joc.6b00904
DO - 10.1021/acs.joc.6b00904
M3 - Article
AN - SCOPUS:84977493171
SN - 0022-3263
VL - 81
SP - 5566
EP - 5573
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 13
ER -