Synlett 2002(8): 1269-1272
DOI: 10.1055/s-2002-32978
LETTER
© Georg Thieme Verlag Stuttgart · New York

Mannich-type Reaction Catalyzed by HBF4 in Water: Effect of the Loading of Surfactant

Takahiko Akiyama*, Junji Itoh, Kohei Fuchibe
Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo 171-8588, Japan
Fax: +81(3)59921029; e-Mail: takahiko.akiyama@gakushuin.ac.jp;
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Publication History

Received 26 May 2002
Publication Date:
25 July 2002 (online)

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Abstract

The HBF4 (0.1 equiv)-catalyzed Mannich-type reactions of ketene silyl acetals with aldimines proceeded smoothly in water in the coexistence of as low as 1 mol% of SDS. Furthermore, the Mannich-type reaction also took place in water in the absence of SDS by means of 0.3 equiv of HBF4 to afford the corresponding β-amino esters in high yields.