Literature DB >> 20571572

Enantioselective iron-catalysed O-H bond insertions.

Shou-Fei Zhu1, Yan Cai, Hong-Xiang Mao, Jian-Hua Xie, Qi-Lin Zhou.   

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.

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Year:  2010        PMID: 20571572     DOI: 10.1038/nchem.651

Source DB:  PubMed          Journal:  Nat Chem        ISSN: 1755-4330            Impact factor:   24.427


  19 in total

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9.  Highly enantioselective insertion of carbenoids into O-H bonds of phenols: an efficient approach to chiral alpha-aryloxycarboxylic esters.

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Journal:  J Am Chem Soc       Date:  2007-09-29       Impact factor: 15.419

10.  Highly enantioselective insertion of carbenoids into N-H bonds catalyzed by copper complexes of chiral spiro bisoxazolines.

Authors:  Bin Liu; Shou-Fei Zhu; Wei Zhang; Chao Chen; Qi-Lin Zhou
Journal:  J Am Chem Soc       Date:  2007-04-12       Impact factor: 15.419

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  20 in total

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4.  Chemoselective Cyclopropanation over Carbene Y-H Insertion Catalyzed by an Engineered Carbene Transferase.

Authors:  Eric J Moore; Viktoria Steck; Priyanka Bajaj; Rudi Fasan
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5.  Enantioselective C-H Olefination of α-Hydroxy and α-Amino Phenylacetic Acids by Kinetic Resolution.

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6.  Iron catalyzed asymmetric oxyamination of olefins.

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Review 9.  Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion.

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10.  Chiral cis-iron(ii) complexes with metal- and ligand-centered chirality for highly regio- and enantioselective alkylation of N-heteroaromatics.

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Journal:  Chem Sci       Date:  2019-11-25       Impact factor: 9.825

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