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Enantioselective Friedel–Crafts Alkylation Reactions of β‐Naphthols with Donor–Acceptor Aminocyclopropanes
Author(s) -
Zhu Man,
Wang DongChao,
Xie MingSheng,
Qu GuiRong,
Guo HaiMing
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804032
Subject(s) - friedel–crafts reaction , enantioselective synthesis , cyclopropane , alkylation , chemistry , kinetic resolution , acceptor , enantiomer , catalysis , enantiomeric excess , organic chemistry , derivative (finance) , medicinal chemistry , ring (chemistry) , physics , condensed matter physics , financial economics , economics
The enantioselective Friedel–Crafts alkylation reaction of β‐naphthols with donor–acceptor aminocyclopropane was developed. In the presence of a copper complex derived from Cu(OTf) 2 and bisoxazoline, a series of γ‐substituted γ‐aminobutyric acid derivatives were obtained with good yields (up to 98 %) and excellent enantioselectivities (up to 98 %). Using this catalytic system, the 2‐amino cyclopropane‐1,1‐dicarboxylate was obtained with high enantiomeric excess (up to 98 %) by an efficient kinetic resolution ( s values of up to 90). The Friedel–Crafts alkylation product could be transformed into a tetracyclic 1,3‐oxazine derivative.