1,2,3-Triazole Bound Au(I) (TA-Au) as Chemoselective Catalysts in Promoting Asymmetric Synthesis of Substituted Allenes

• DOI: 10.1021/ol200714h
• Publication Date: 2011-04-19T17:10:30Z
• Authors: Dawei Wang; Lekh Nath S. Gautam; Cynthia Bollinger; Aleksandra Harris; Minyong Li; Xiaodong Shi
• Keywords: Propargyl; Racemization; Cationic polymerization; Triazole; Chirality

The triazole-Au (TA-Au) complexes were identified as effective chemoselective catalysts in promoting propargyl ester/ether 3,3-rearrangements. highly reactive allenes, which could not be isolated by simple cationic gold catalysts, prepared excellent yields (1% catalyst loading, >90% yields). Unlike other reported Au the TA-Au provided chirality transfer without racemization over a long period of time, giving enantioenriched allenes with stereoselectivity up to 99% ee).