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Catalysis of Mukaiyama Aldol Reactions by a Tricyclic Aluminum Alkoxide Lewis Acid

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posted on 07.08.2009, 00:00 by Steven M. Raders, John G. Verkade
The Mukayiama aldol reaction of aldehydes is efficiently accomplished with a low concentration of the dimeric alumatrane catalyst 2 at mild or subambient temperatures. Our protocol tolerates a wide variety of electron-rich, neutral, and deficient aryl, alkyl, and heterocyclic aldehydes. A wide variety of enol silyl ethers are also tolerated. An intermediate that was isolated provides mechanistic information regarding the role of dimeric 2 in the Mukaiyama aldol reaction. Experimental evidence is presented for the stronger Lewis acidity of 5 compared with F3B.