ChemInform Abstract: Highly Enantioselective Formation of α‐Allyl‐α‐arylcyclopentanones via Pd‐Catalyzed Decarboxylative Asymmetric Allylic Alkylation.

• DOI: 10.1002/chin.201649028
• Publication Date: 2016-11-17T08:56:38Z
• Authors: Ramulu Akula; Robert Doran; Patrick J. Guiry
• Keywords: 01 natural sciences; 0104 chemical sciences

AbstractA highly enantioselective Pd‐catalysed decarboxylative asymmetric allylic alkylation of cyclopentanone derived α‐aryl‐β‐keto esters employing the (R,R)‐ANDEN‐phenyl Trost ligand has been developed. The product (S)‐α‐allyl‐α‐arylcyclopentanones were obtained in excellent yields and enantioselectivities (up to >99.9 % ee). This represents one of the most highly enantioselective formations of an all‐carbon quaternary stereogenic center reported to date. This reaction was demonstrated on a 4.0 mmol scale without any deterioration of enantioselectivity and was exploited as the key enantioselective transformation in an asymmetric formal synthesis of the natural product (+)‐tanikolide.