Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom