Aldol Synthesis with an Aqueous Solution of Formalin

Nobuko Ozasa; Manabu Wadamoto; Kazuaki Ishihara; Hisashi Yamamoto

doi:10.1055/s-2003-42089

LETTER

Aldol Synthesis with an Aqueous Solution of Formalin

Nobuko Ozasa^a, Manabu Wadamoto^b, Kazuaki Ishihara^a, Hisashi Yamamoto*^b
^a Graduate School of Engineering, Nagoya University, SORST, Japan Science and Technology Corporation (JST), , Chikusa, Nagoya 464-8603, Japan
^b Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637, USA
Fax: +1(773)7020805; e-Mail: yamamoto@uchicago.edu;

Abstract

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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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References

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The reaction mixture is barely stirrable without being unfrozen.