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Catalytic Asymmetric Intramolecular [4+2] Cycloaddition of In Situ Generated ortho ‐Quinone Methides
Author(s) -
Xie Youwei,
List Benjamin
Publication year - 2017
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.201612149
Subject(s) - intramolecular force , cycloaddition , catalysis , chemistry , quinone , quinone methide , in situ , photochemistry , combinatorial chemistry , organic chemistry
Herein, we describe the first catalytic asymmetric intramolecular [4+2] cycloaddition of in situ generated ortho‐quinone methides. In the presence of a confined chiral imidodiphosphoric acid catalyst, various salicylaldehydes react with dienyl alcohols to give transient ortho ‐quinone methide intermediates, which undergo an intramolecular [4+2] cycloaddition to provide highly functionalized furanochromanes and pyranochromanes in excellent diastereoselectivity and enantioselectivity.