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Synlett 2003(14): 2219-2221
DOI: 10.1055/s-2003-42089
DOI: 10.1055/s-2003-42089
LETTER
© Georg Thieme Verlag Stuttgart · New York
Aldol Synthesis with an Aqueous Solution of Formalin
Further Information
Received
2 May 2003
Publication Date:
15 October 2003 (online)
Publication History
Publication Date:
15 October 2003 (online)
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Abstract
With an aqueous solution of formalin, aldol reaction of trimethylsilyl enol ether proceeds moderately using tetrabutylammonium fluoride (TBAF). Furthermore, catalytic asymmetric hydroxymethylation with trimethoxysilyl enol ether using water tolerant (R)-BINAP-AgOTf as Lewis acid and KF as Lewis base has been achieved in aqueous media.
Key words
aldol reaction - silyl enol ether - enantioselective - BINAP-AgOTf catalyst - formalin aqueous solution
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3a Fluoride mediated aldol synthesis using silyl enol ethers:
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3e See also:
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References
The reaction mixture is barely stirrable without being unfrozen.