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Synfacts 2011(2): 0133-0133
DOI: 10.1055/s-0030-1259385
DOI: 10.1055/s-0030-1259385
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Enantioselective Synthesis of Dihydrofurans Using Dynamic Kinetic Resolution
S. Lin, G.-L. Zhao*, L. Deiana, J. Sun, Q. Zhang, H. Leijonmarck, A. Córdova*
Stockholm University, Royal institute of Technology, Stockholm and Mid Sweden University, Sundsvall, Sweden
Further Information
Publication History
Publication Date:
19 January 2011 (online)
Significance
The synthesis of dihydrofurans via a dynamic kinetic asymmetric domino oxa-Michael-carbocyclization procedure is reported. The optimization of the reaction parameters (solvent, temperature, metal source, additives, organocatalyst) is described. The requirements for both a metal catalyst and a proline-derived organocatalyst for the transformation were established. Although aryl substitution in the aldehyde component was well tolerated, aliphatic aldehydes were found to give lower yields. The use of secondary and tertiary propargylic alcohols was also shown to afford good enantioselectivity, but poor diastereoselectivity.