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Enantioselective Synthesis of Medium‐Sized‐Ring Lactones by Organocatalytic Michael Addition Followed by Reductively Initiated Fragmentation
Author(s) -
Roudier Mylène,
Constantieux Thierry,
Quintard Adrien,
Rodriguez Jean
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500894
Subject(s) - enantioselective synthesis , cycloalkane , ring (chemistry) , chemistry , organocatalysis , fragmentation (computing) , michael reaction , catalysis , stereochemistry , combinatorial chemistry , organic chemistry , computer science , operating system
A new strategy for the rapid synthesis of enantioenriched medium‐sized‐ring lactones was developed. The method combines the organocatalytic Michael addition of cycloalkane‐1,3‐diones to α,β‐unsaturated aldehydes with a subsequent reductively initiated Claisen fragmentation, which allows access to 10‐ and 11‐membered‐ring lactones with 91 to >99 % ee .