Author: ["Shou-Fei Zhu","Yan Cai","Hong-Xiang Mao","Jian-Hua Xie","Qi-Lin Zhou"]
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Abstract
The ready availability, low price and environmentally benign character of iron mean that it is an ideal alternative to precious metals in catalysis. Recent growth in the number of iron-catalysed reactions reported reflects an increasing demand for sustainable chemistry. Only a limited number of chiral iron catalysts have been reported and these have, in general, proven less enantioselective than other transition-metal catalysts, thus limiting their appeal. Here, we report that iron complexes of spiro-bisoxazoline ligands are highly efficient catalysts for asymmetric O–H bond insertion reactions. These complexes catalyse insertions into the O–H bond of a wide variety of alcohols and even water, with exceptional enantioselectivities under mild reaction conditions. The selectivities surpass those obtained with other transition-metal catalysts. This study should inspire and encourage the use of iron instead of traditional precious metals in the development of greener catalysts for catalytic asymmetric synthesis. Iron is an abundant, low cost and environmentally benign metal. Here, iron complexes are shown to be the most effective catalysts for asymmetric O–H insertion reactions. These results should encourage the use of iron, rather than more traditional precious metals, in the development of greener organometallic catalysts for asymmetric transformations.Cite this article
Zhu, SF., Cai, Y., Mao, HX. et al. Enantioselective iron-catalysed O–H bond insertions. Nature Chem 2, 546–551 (2010). https://doi.org/10.1038/nchem.651 