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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 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.201510972
Subject(s) - protonation , chemistry , enantioselective synthesis , conjugate , prins reaction , catalysis , cascade , combinatorial chemistry , brønsted–lowry acid–base theory , cascade reaction , organocatalysis , 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.
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