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Synfacts 2007(11): 1169-1169  
DOI: 10.1055/s-2007-991251
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Enantioselective Synthesis of 4-Aryl-4H-chromenes

Contributor(s): Mark Lautens, Praew Thansandote
T. Nishikata, Y. Yamamoto, N. Miyaura*
Innovation Plaza Hokkaido Science and Technology Agency and Hokkaido University, Sapporo, Japan
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Publication History

Publication Date:
23 October 2007 (online)

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Significance

A palladium-catalyzed asymmetric 1,4-addition is used as a novel method for the preparation of enantioenriched 4-arylchromanols and 4-aryl-4H-chromenes. Baeyer-Villiger oxidation of the 1,4-addition product leads to 4-aryl­chroma­nones. A wide variety of aryl boronic acids and β-arylenones were used and the high yields and excellent enantioselectivities observed make the current method a good choice for generating a library of enantiopure chromene analogues.