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 versatile building blocks that can readily be converted to synthetically useful materials.

[1]  M. Lautens,et al.  Modular and stereoselective synthesis of tetrasubstituted helical alkenes via a palladium-catalyzed domino reaction. , 2012, Organic letters.

[2]  S. Suga,et al.  Kinetic resolution of secondary alcohols by the combination of a chiral Brønsted acid, DABCO, and acetyl chloride. , 2012, Organic letters.

[3]  M. Rueping,et al.  Chiral Brønsted acids in enantioselective carbonyl activations--activation modes and applications. , 2011, Chemical Society reviews.

[4]  V. B. Birman,et al.  Dynamic kinetic resolution of azlactones catalyzed by chiral Brønsted acids. , 2011, Organic letters.

[5]  K. Ishihara,et al.  Which is the actual catalyst: chiral phosphoric Acid or chiral calcium phosphate? , 2010, Angewandte Chemie.

[6]  A. Minnaard,et al.  Copper-Catalyzed Asymmetric Allylic Alkylation of Halocrotonates: Efficient Synthesis of Versatile Chiral Multifunctional Building Blocks , 2010 .

[7]  S. Ley,et al.  Total synthesis of the anti-apoptotic agents iso- and bongkrekic acids. , 2010, Organic letters.

[8]  A. Ghanem.  Trends in lipase-catalyzed asymmetric access to enantiomerically pure/enriched compounds , 2007 .

[9]  T. Akiyama,et al.  Recent Progress in Chiral Brønsted Acid Catalysis , 2006 .

[10]  M. Terada,et al.  Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation. , 2004, Journal of the American Chemical Society.

[11]  Junji Itoh,et al.  Enantioselective Mannich-type reaction catalyzed by a chiral Brønsted acid. , 2004, Angewandte Chemie.

[12]  Yong Huang,et al.  Hydrogen bonding: Single enantiomers from a chiral-alcohol catalyst , 2003, Nature.

[13]  P. Váchal,et al.  Structure-based analysis and optimization of a highly enantioselective catalyst for the strecker reaction. , 2002, Journal of the American Chemical Society.

[14]  Nick A. Paras,et al.  New strategies in organic catalysis: the first enantioselective organocatalytic Friedel-Crafts alkylation. , 2001, Journal of the American Chemical Society.

[15]  Eric N. Jacobsen,et al.  SCHIFF BASE CATALYSTS FOR THE ASYMMETRIC STRECKER REACTION IDENTIFIED AND OPTIMIZED FROM PARALLEL SYNTHETIC LIBRARIES , 1998 .

[16]  E. Santaniello,et al.  Lipase-catalyzed transesterification in organic solvents: Applications to the preparation of enantiomerically pure compounds , 1993 .

[17]  I. Alfonso,et al.  Enantioselective enzymatic desymmetrizations in organic synthesis. , 2005, Chemical reviews.