The synthesis of HMF-based α-amino phosphonates via one-pot Kabachnik-Fields reaction.

ABSTRACT: The first use of biomass-derived HMF in the one-pot Kabachnik-Fields reaction is reported here. A wide range of furan-based α-amino phosphonates were prepared in moderate to excellent yields under mild, effective and environmentally-benign conditions: iodine as a non-metal catalyst, biobased 2-MeTHF as the solvent and room or moderate temperature. The hydroxymethyl group of HMF persists in the Kabachnik-Fields products, widening the scope of further modification and derivatization compared to those arising from furfural. Issues involving the diastereoselectivity and double Kabachnik-Fields condensation were also faced.

SUBMITTER: Fan W 

PROVIDER: S-EPMC9085609 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature