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. 2011 Aug 24;133(33):12972-5.
doi: 10.1021/ja205068j. Epub 2011 Jul 28.

Chiral (acyclic diaminocarbene)gold(I)-catalyzed dynamic kinetic asymmetric transformation of propargyl esters

Yi-Ming Wang  1 , Christian N Kuzniewski, Vivek Rauniyar, Christina Hoong, F Dean Toste
Affiliations

Chiral (acyclic diaminocarbene)gold(I)-catalyzed dynamic kinetic asymmetric transformation of propargyl esters

Yi-Ming Wang et al. J Am Chem Soc. .

Abstract

A highly enantioselective transformation catalyzed by chiral (acyclic diaminocarbene)gold(I) complexes is reported. The enantioselective synthesis of 2-substituted chromenyl pivalates from racemic phenol-substituted propargyl pivalates was developed. Rearrangement of the substrates in the presence of cationic gold gave allene intermediates, whose cyclization resulted in formation of enantioenriched product through a dynamic kinetic asymmetric transformation.

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