Organic Chemistry: Current Research
Open Access

Enantioselective trapping of oxonium ylide with N-Benzhydryl-α-imino ester: A rapid access to synthesis of β-tetra substituted α-amino acids

International Conference on Organic Chemistry

August 10-11, 2016 Las Vegas, Nevada, USA

Shunying Liu, Yubing Lei, Shikun Jia and Wenhao Hu

East China Normal University, China

Scientific Tracks Abstracts: Organic Chem Curr Res

Abstract :

�²-Alkoxy C�²-tetrasubstituted �±-amino acid derivatives are commonly serviceable structural motifs in biologically active natural products and pharmaceuticals. Several efficient methods have been established to construct �²-tetrasubstituted �±-amino acids. Nevertheless, a rapid access to construction of these complex molecules from simple starting materials under mild conditions are urgently in demand. Multi-component reactions (MCRs) have provided such an approach to realize this goal. Here, a synergistic rhodium(II)/phosphoric acid catalyzed three component reaction of 3-diazooxindoles, alcohols and N-benzhydryl-�±-imino ester is successfully developed to provide an efficient strategy for the rapid construction of chiral �²-alkoxy C�²-tetrasubstituted �±-amino acid derivatives with high diastereoselectivity (up to 20:1 dr) and excellent enantioselectivity (up to 98:2 er) from simple starting points under mild conditions (Scheme 1). The resulting multi-component products 4 readily afforded 3-spirocyclic oxindole 5 under the standard hydrogenation conditions followed a cyclization with CSCl2 in a good yield remaining excellent enantioselectivity.

Biography :

Shunying Liu has completed her PhD from Wuhan University and Post-doctoral studies from Hong Kong Baptist University and Oxford University. Her research interest is mainly on asymmetric catalysis for multi-component reaction. She has published more than 50 papers in reputed journals.

Email: syliu@sist.ecnu.edu.cn