An organocatalytic enantioselective Mannich-type reaction of isocyanoacetate with N-sulfonylimines catalyzed by chiral thioureas derived from quinine yielded 2-imidazolines with high diastereo- and enantioselectivities (up to >99:1 dr. and 96% ee). This reaction provided a convenient route to access various imidazolines and related α,β-diamino acids having a quaternary carbon center in high enantiomeric purities.
and stereoselective method to prepare imidazolines bearing quaternary centers is reported. The nature of imine substituent and ester group has influence on the stereoselective outcome. The imidazolines can smoothly be converted into α,β-diamino esters. -(NAKAMURA*, S.; MAENO, Y.; OHARA, M.; YAMAMURA, A.; FUNAHASHI, Y.; SHIBATA, N.; Org. Lett. 14 (2012) 12, 2960-2963, http://dx.doi.org/10.1021/ol301256q ; Dep. Front. Mater., Grad. Sch. Eng., Nagoya Inst. Technol., Showa, Nagoya 466, Japan; Eng.) -Jannicke 41-129
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