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Modular Synthesis of Triazole‐Based Chiral Iodoarenes for Enantioselective Spirocyclizations
Author(s) -
Hempel Christian,
MaichleMössmer Caeciliea,
Pericàs Miquel A.,
Nachtsheim Boris J.
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700246
Subject(s) - chemistry , enantiopure drug , enantioselective synthesis , hypervalent molecule , enantiomer , combinatorial chemistry , kinetic resolution , azide , click chemistry , alkyne , triazole , 1,2,3 triazole , stereochemistry , organic chemistry , catalysis , reagent
A new triazole‐based C 1 ‐symmetrical chiral iodoarene was synthesized in a highly modular route. Based on enzymatic kinetic resolution of an easily accessible propargylic alcohol both enantiomers were accessible in enantiopure form. By Huisgen‐type azide‐alkyne cycloaddtion a series of differently substituted iodoarenes was synthesized in high overall yields. Finally this novel iodoarene was successfully applied in the oxidative Kita cyclization of naphthol derivatives. Good yields and high ee values were obtained in the asymmetric spirocyclization via in situ generation of the hypervalent iodine species using m CPBA as the terminal oxidant.