Asymmetric Diels-Alder Reaction of alpha,beta-Unsaturated Oxazolidin-2-one Derivatives Catalyzed by a Chiral Fe(III)-Bipyridine Diol Complex

作者：Li Mao; Carreras Virginie; Jalba Angela; Ollevier Thierry^*

来源：Organic Letters, 2018, 20(4): 995-998.

DOI：10.1021/acs.orglett.7b03939

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An asymmetric Fe-III-bipyridine diol catalyzed Diels-Alder reaction of alpha,beta-unsaturated oxazolidin-2-ones has been developed. Among various Fe-II/Fe-III salts, Fe(ClO4)(3)center dot 6H(2)O was selected as the Lewis acid of choice. The use of a low catalyst loading (2 mol % of Fe(ClO4)(3)center dot 6H(2)O and 2.4 mol % of Bolm's ligand) afforded high yields (up to 99%) and high enantiomeric excesses (up to 98%) of endo-cycloadducts for the Diels-Alder reaction between cyclopentadiene and substituted acryloyloxazolidin-2-ones. Other noncyclic dienes led to decreased enantioselectivities. A proposed model supports the observed stereoinduction.

• 出版日期2018-2-16