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Synthesis of isochromans via Fe(OTf)2-catalyzed Oxa-Pictet–Spengler cyclization

Author:
Zhou, Jimei, Wang, Chao, Xue, Dong, Tang, Weijun, Xiao, Jianliang, Li, Chaoqun
Source:
Tetrahedron 2018 v.74 no.49 pp. 7040-7046
ISSN:
0040-4020
Subject:
aldehydes, byproducts, catalysts, catalytic activity, chemical structure, cyclization reactions, iron
Abstract:
Fe(OTf)2 has been found to be an efficient catalyst for the Oxa-Pictet–Spengler cyclization reaction leading to isochromans. A series of substituted isochromans were obtained with good to excellent isolated yields by coupling β-arylethanols with aldehydes or ketals under the catalysis of 1 mol% of Fe(OTf)2 at 70 °C. Using a cheap, less-toxic catalyst with water as the only byproduct, this iron-catalyzed Oxa-Pictet–Spengler reaction can be considered environmentally-friendly and atom-economic.
Agid:
6176271