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Expedient and Diastereodivergent Assembly of Terpenoid Decalin Subunits having Quaternary Stereocenters through Organocatalytic Robinson Annulation of Nazarov Reagent
Author(s) -
Berkes Barbara,
Ozsváth Kristóf,
Molnár Laura,
Gáti Tamás,
Holczbauer Tamás,
Kardos György,
Soós Tibor
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604541
Subject(s) - stereocenter , annulation , reagent , chemistry , organocatalysis , decalin , terpenoid , stereochemistry , catalysis , combinatorial chemistry , organic chemistry , enantioselective synthesis
We report an expedient approach to highly functionalized cis ‐ and trans ‐decalines that could function as key structural subunits toward the synthesis of various classes of terpenoids. Key to the strategy is an organocatalyzed Robinson annulation reaction of the Nazarov reagent that affords chiral enone building blocks with high enantioselectivities. The quaternary carbon stereogenic center can direct the subsequent reactions and allow the rapid and diastereoconvergent assembly of complex decalines with contiguous stereocenters.