Premium
Controlling the Molecular Topology of Vinylogous Iminium Ions by Logical Substrate Design: Highly Regio‐ and Stereoselective Aminocatalytic 1,6‐Addition to Linear 2,4‐Dienals
Author(s) -
Silvi Mattia,
Chatterjee Indranil,
Liu Yiankai,
Melchiorre Paolo
Publication year - 2013
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.201305870
Subject(s) - iminium , stereoselectivity , topology (electrical circuits) , substrate (aquarium) , chemistry , tetrahydrofuran , trimethylsilyl , ion , position (finance) , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , mathematics , combinatorics , oceanography , finance , solvent , economics , geology
All about topology control : The title reaction yields valuable tetrahydrofuran spirooxindoles (see scheme; TMS=trimethylsilyl), and exemplifies a rare asymmetric 1,6‐addition to linear 2,4‐dienals proceeding with high δ‐site‐ and stereoselectivity. A steering group at the β‐dienal position ensured molecular preorganization of the catalytically active vinylogous iminium ion intermediate for highly predictable reaction outcomes.