Racemic Morita-Baylis-Hillman adducts derived from the reaction of acrylonitrile with benzaldehyde, cinnamaldehyde and hydrocinnamaldehyde have been successfully resolved by means of enzymatic kinetic resolution. The (+)-alcohol products were isolated with 94–97% ee after lipase-mediated enantioselective hydrolysis of the corresponding acetates. Mosher’s double derivatisation protocol was applied to these isolated products and the absolute configuration of the alcohols was found to be (S) for all three substrates.
Reference:
Juma, W.P. et al. 2017. Enzymatic kinetic resolution of Morita-Baylis-Hillman acetates. Tetrahedron: Asymmetry, vol. 28(9): 1169-1174
Juma, W., Chhiba, V. P., Brady, D., & Bode, M. (2017). Enzymatic kinetic resolution of Morita-Baylis-Hillman acetates. http://hdl.handle.net/10204/9781
Juma, WP, Varsha P Chhiba, D Brady, and ML Bode "Enzymatic kinetic resolution of Morita-Baylis-Hillman acetates." (2017) http://hdl.handle.net/10204/9781
Juma W, Chhiba VP, Brady D, Bode M. Enzymatic kinetic resolution of Morita-Baylis-Hillman acetates. 2017; http://hdl.handle.net/10204/9781.
Copyright: 2017 Elsevier. Due to copyright restrictions, the attached PDF file only contains the pre-print version of the published article. For access to the published item, please consult the publisher's website.
