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Anionic–Anionic Asymmetric Tandem Reactions: One‐Pot Synthesis of Optically Pure Fluorinated Indolines from 2‐ p ‐Tolylsulfinyl Alkylbenzenes
Author(s) -
García Ruano José Luis,
Alemán José,
Catalán Silvia,
Marcos Vanesa,
Monteagudo Silvia,
Parra Alejandro,
del Pozo Carlos,
Fustero Santos
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200802885
Subject(s) - nucleophilic aromatic substitution , stereocenter , chemistry , alkylbenzenes , intramolecular force , stereoselectivity , tandem , nucleophilic substitution , chirality (physics) , nucleophile , stereochemistry , combinatorial chemistry , leaving group , enantioselective synthesis , medicinal chemistry , organic chemistry , catalysis , materials science , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark , composite material
Chirality switch up : A novel strategy has been developed to give optically pure fluorinated indolines with one or two stereogenic centers (see scheme; A N =nucleophilic addition, PG=protecting group, S N Ar=intramolecular nucleophilic aromatic substitution, Tol=tolyl). Almost complete stereoselectivity and mild reaction conditions are the key features of the title reaction.