Enantioselective Addition of Ketene Silyl Acetals to Nitrones Catalyzed by Chiral Titanium Complexes. Synthesis of Optically Active β-Amino Acids
Journal of the American Chemical Society2002Vol. 124(12), pp. 2888–2889
Citations Over TimeTop 10% of 2002 papers
Shun‐Ichi Murahashi, Yasushi Imada, Toru Kawakami, Kazuhito Harada, Yoshiharu Yonemushi, Naomi Tomita
Abstract
A chiral titanium complex, Ti(O-i-Pr)(4)/BINOL/tert-butylcatechol, catalyzes enantioselective addition reaction of ketene silyl acetals to nitrones to give optically active beta-amino acid derivatives which are biologically active compounds and useful synthetic intermediates of natural products and pharmaceuticals such as beta-lactam antibiotics. The combined process of catalytic oxidation of secondary amines and enantioselective carbon-carbon bond formation of nitrones thus obtained with ketene silyl acetals provides a useful two-step method for the synthesis of optically active beta-amino acid derivatives and related nitrogen compounds.
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