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Synfacts 2006(1): 0069-0069  
DOI: 10.1055/s-2005-921715
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

TADDOL-Derived Phosphoric Acid Catalyst

Contributor(s): Benjamin List, Sonja Mayer
T. Akiyama*, Y. Saitoh, H. Morita, K. Fuchibe
Gakushuin University, Japan
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Publication History

Publication Date:
16 December 2005 (online)

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Significance

TADDOL phosphoric acid derivatives (3) were synthesized from (+)-diethyl tartrate and used as novel chiral Brønsted acid organocatalysts with different electronic and steric properties compared to the known BINOL-derived Brønsted acids. The catalysts were employed in a Mannich-type reaction with 5 mol% catalyst loading. Different aldimines (1) and ketene silyl acetales (2) were used to give the corresponding β-amino esters (4) in good to excellent yields (47-97%) and up to 92% ee.