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Synfacts 2011(10): 1136-1136
DOI: 10.1055/s-0030-1261084
DOI: 10.1055/s-0030-1261084
Polymer-Supported Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Asymmetric Aldol Reactions in Brine with Fluorous Organocatalysts
T. Miura*, K. Imai, H. Kasuga, M. Ina, N. Tada, N. Imai, A. Itoh
Gifu Pharmaceutical University and Chiba Institute of Science, Japan
Further Information
Publication History
Publication Date:
20 September 2011 (online)
Significance
Homochiral fluorous β-aminosulfonamide 3 was prepared from 1 via condensation with C8F17SO2F, followed by deprotection of the N-Boc group (eq. 1). Sulfonamide 3 promoted the direct asymmetric aldol reaction of aldehydes 4 with ketones 5 in brine to give the corresponding anti-aldol products 6 in up to 100% yield with 25-96% ee (17 examples, eq. 2).