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Organocatalytic Enantioselective Friedel–Crafts Reaction of 1‐Naphthols with Isatins and an Unexpected Spontaneous Dehydration Process
Author(s) -
Wu Deyan,
Zhang Xuwen,
Xu Yong,
Xue Yingfei,
Li Jian,
Wang Wei,
Zhu Jin
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300170
Subject(s) - chemistry , enantioselective synthesis , friedel–crafts reaction , cinchona , intramolecular force , cinchona alkaloids , organic chemistry , organocatalysis , ketone , thiourea , alkylation , catalysis , dehydration , biochemistry
An organocatalytic enantioselective Friedel–Crafts alkylation of 1‐naphthols with isatins has been developed. The process is catalyzed by a simple cinchona alkaloid derived thiourea and gives biologically interesting, enantioenriched 3‐(naphthalen‐2‐yl)‐3‐hydroxy‐2‐oxindoles in moderate to good yields of 42–83 % and with good to high enantioselectivity of up to 94 % ee . Furthermore, an unexpected intramolecular dehydration reaction proceeds spontaneously with 4‐substituted 1‐naphthols to offer structurally different ketone oxindoles.