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Enantioselective Synthesis of γ‐Functionalized Cyclopentenones and δ‐Functionalized Cycloheptenones Utilizing a Redox‐Relay Heck Strategy
Author(s) -
Yuan Qianjia,
Prater Matthew B.,
Sigman Matthew S.
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901239
Subject(s) - chemistry , desymmetrization , enantioselective synthesis , heck reaction , combinatorial chemistry , aryl , yield (engineering) , indole test , organic chemistry , catalysis , alkyl , materials science , metallurgy
In this report, the desymmetrization of cyclic enones under relay Heck conditions with an array of aryl boronic acids, alkenyl triflates and indole derivatives is described. This method grants facile access to diverse γ‐functionalized cyclopentenones and δ‐functionalized cycloheptenones. Using this approach, a formal synthesis of ( S )‐baclofen was completed in high yield and excellent enantioselectivity.