Enantioselective Synthesis of Medium‐Sized‐Ring Lactones by Organocatalytic Michael Addition Followed by Reductively Initiated Fragmentation | Zendy

Roudier Mylène | Zendy; Constantieux Thierry | Zendy; Quintard Adrien | Zendy; Rodriguez Jean | Zendy

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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 .

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