Facile Synthesis of Versatile Enantioenriched α‑Substituted Hydroxy Esters through a Brønsted Acid Catalyzed Kinetic Resolution

An efficient synthesis of enantioenriched α-substituted γ-hydroxy esters via a kinetic resolution event is described. Bulky racemic esters in the presence of a chiral Brønsted acid selectively lactonize to yield a recoverable enantioenriched hydroxy ester and lactone. These esters are highly versati...

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Veröffentlicht in:Organic letters 2013-03, Vol.15 (6), p.1266-1269
Hauptverfasser: Qabaja, Ghassan, Wilent, Jennifer E, Benavides, Amanda R, Bullard, George E, Petersen, Kimberly S
Format: Artikel
Sprache:eng
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Zusammenfassung:An efficient synthesis of enantioenriched α-substituted γ-hydroxy esters via a kinetic resolution event is described. Bulky racemic esters in the presence of a chiral Brønsted acid selectively lactonize to yield a recoverable enantioenriched hydroxy ester and lactone. These esters are highly versatile building blocks that can readily be converted to synthetically useful materials.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400207t