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Synfacts 2006(7): 0725-0725  
DOI: 10.1055/s-2006-941910
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Intramolecular Crossed Aldehyde-Ketone Benzoin Cyclization

Contributor(s): Benjamin List, Subhas Chandra Pan
H. Takikawa, Y. Hachisu, J. W. Bode, K. Suzuki*
Tokyo Institute of Technology, Japan
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

Here the authors report an enantio­selective intramolecular aldehyde-ketone benzoin cyclization. Rovis’ aminoindanol-derived triazolium salt 1 (J. Am. Chem. Soc. 2005, 127, 6284-6289) in combination with DBU has been found to be effective for the reaction. With 10-25 mol% of 1, moderate to high yields (44-91%) and enantio­selectivities (39-99%) are obtained for a wide variety of substrates.