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Enantio‐ and Diastereoselective Synthesis of exo ‐Peroxyacetals: An Organocatalyzed Peroxyhemiacetalization/oxa‐Michael Addition Cascade
Author(s) -
Maity Sanjay,
Parhi Biswajit,
Ghorai Prasanta
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201511165
Subject(s) - enantioselective synthesis , bifunctional , moiety , chemistry , nucleophile , michael reaction , cinchona , organocatalysis , peroxide , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
An unprecedented enantioselective peroxyhemiacetalization/oxa‐Michael addition cascade of ortho ‐formyl homochalcones has been developed using cinchona‐alkaloid‐based chiral bifunctional organocatalysts to provide cis ‐configured exo ‐peroxyacetals, a new class of organic peroxide, in good yields with excellent enantio‐ and diastereoselectivities. The resulting cis ‐configured exo ‐peroxyacetals were converted into the corresponding trans ‐configured peroxyacetals without affecting the enantioselectivity. Furthermore, the displacement of the peroxide moiety of exo ‐peroxyacetals with various nucleophiles has been demonstrated to afford 1,3‐disubstituted isochromans with high diastereoselectivities and excellent enantioselectivities.