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Highly Stereoselective Synthesis of trans ‐3‐Aryl‐4‐carbethoxy‐2,3‐dihydro‐2‐fur‐2′‐oyl‐5‐methylfurans
Author(s) -
Zhang Hui,
Cao WeiGuo,
Chen Jie,
Hu JiRong,
Qian JiaXian,
Zhu ShiZheng
Publication year - 2007
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200790188
Subject(s) - chemistry , stereoselectivity , yield (engineering) , aryl , tetrahydrofuran , regioselectivity , bromide , stereochemistry , combinatorial chemistry , organic chemistry , solvent , alkyl , catalysis , materials science , metallurgy
Multi‐substituted dihydrofurans are valuable intermediates for the synthesis of natural products and pharmaceuticals. Considerable attention has been focused on the development of efficient and regioselective methods for their preparation. Using K 2 CO 3 as a base, with the reaction of fur‐2‐oylmethyltriphenylarsonium bromide 1 and ethyl 2‐acetyl‐3‐arylacrylate 2 in tetrahydrofuran at room temperature, we found an efficient protocol was achieved to synthesize trans ‐3‐aryl‐4‐carbethoxy‐2,3‐dihydro‐2‐fur‐2′‐oyl‐5‐methylfurans 3 in good yield with high stereoselectivity. The structure of compound 3 was confirmed by IR, 1 H NMR, MS and HRMS. The mechanism for the formation of 3 was proposed.