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- W2086784361 abstract "Abstract New methodology for the stereoselective synthesis of trisubstituted olefins is presented. The use of ortho ‐diphenylphosphanyl benzoate ( o ‐DPPB) as a directing leaving group for copper‐mediated allylic substitution with Grignard reagents allowed for the stereoselective construction of a wide range of E olefins, without the need for an adjacent electron‐withdrawing group. Our modular three‐step approach toward trisubstituted alkenes commenced with geminal α‐methylene aldehydes. Addition of an organometallic reagent and introduction of the o ‐DPPB group by esterification was followed by the o ‐DPPB‐directed copper‐mediated allylic substitution with a Grignard reagent to furnish stereodefined trisubstituted olefins. Additionally, incorporation of a stereocenter from the chiral pool allowed the preparation of an enantiomerically pure olefin that bore three alkyl substituents in high E / Z selectivity." @default.
- W2086784361 created "2016-06-24" @default.
- W2086784361 creator A5067624195 @default.
- W2086784361 creator A5075153084 @default.
- W2086784361 date "2011-09-02" @default.
- W2086784361 modified "2023-10-18" @default.
- W2086784361 title "Stereoselective Synthesis of Trisubstituted Olefins by a Directed Allylic Substitution Strategy" @default.
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- W2086784361 doi "https://doi.org/10.1002/chem.201100843" @default.
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