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Synthesis of Enantioenriched Indolines by a Conjugate Addition/Asymmetric Protonation/Aza‐Prins Cascade Reaction
Author(s) -
Daniels Blake E.,
Ni Jane,
Reisman Sarah E.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201510972
Subject(s) - protonation , chemistry , enantioselective synthesis , prins reaction , conjugate , catalysis , cascade , brønsted–lowry acid–base theory , combinatorial chemistry , cascade reaction , lewis acids and bases , organic chemistry , ion , mathematical analysis , mathematics , chromatography
A conjugate addition/asymmetric protonation/aza‐Prins cascade reaction has been developed for the enantioselective synthesis of fused polycyclic indolines. A catalyst system generated from ZrCl 4 and 3,3′‐dibromo‐BINOL enables the synthesis of a range of polycyclic indolines in good yields and with high enantioselectivity. A key finding is the use of TMSCl and 2,6‐dibromophenol as a stoichiometric source of HCl to facilitate catalyst turnover. This transformation is the first in which a ZrCl 4 ⋅BINOL complex serves as a chiral Lewis‐acid‐assisted Brønsted acid.