PMID: 11902876Mar 21, 2002Paper

Enantioselective addition of ketene silyl acetals to nitrones catalyzed by chiral titanium complexes. Synthesis of optically active beta-amino acids

Journal of the American Chemical Society
Shun-ichi MurahashiNaomi 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.

Citations

Sep 30, 2009·Chemical Communications : Chem Comm·Mikiko Sodeoka, Yoshitaka Hamashima
May 12, 2011·Proceedings of the Japan Academy. Series B, Physical and Biological Sciences·Shun-Ichi Murahashi
Aug 25, 2006·Organic Letters·Sa Wang, Christopher T Seto
Sep 22, 2005·Angewandte Chemie·Mark S TaylorEric N Jacobsen
Sep 20, 2012·Angewandte Chemie·Imants KreitussJeffrey W Bode
Dec 15, 2010·Organic & Biomolecular Chemistry·Martina CacciariniStefano Roelens
May 21, 2010·Organic Letters·Sa WangChristopher T Seto
Mar 10, 2005·Chemical Reviews·Jean Michel Brunel
Mar 16, 2019·Chemical Reviews·Shun-Ichi Murahashi, Yasushi Imada

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