Synfacts 2011(4): 0454-0454  
DOI: 10.1055/s-0030-1259741
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Aldol and α-Amination Reactions with Proline-Functionalized Reactors

Contributor(s): Yasuhiro Uozumi, Haifeng Zhou
A. Massi*, A. Cavazzini*, L. De Zoppo, O. Pandoli, V. Costa, L. Pasti, P. P. Giovannini
Università di Ferrara, Italy and Shanghai Jiao Tong University, P. R. of China
Further Information

Publication History

Publication Date:
18 March 2011 (online)

Significance

Proline-functionalized silica 1 was synthesized and the packed-bed reactor A was developed by filling with 1. Continuous-flow aldol reaction of cyclohexanone 2 with 4-nitrobenzaldehyde 3 proceeded at 5 mL min flow rate to give 4 with 4:1 dr (anti/syn) and 78% ee of the anti isomer. The α-amination reaction of isovaleraldehyde 5 with dibenzylazodicarboxylate 6 was also performed using the reactor A at 25 mL min flow rate to give 7 with >95% conversion, 55% ee, and 3.60 mmol h mmolcat productivity.