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- W3152966822 abstract "This study demonstrates that chiral-at-iron complexes, in which all coordinated ligands are achiral and the overall chirality the consequence of a stereogenic iron center, are capable of catalyzing asymmetric transformations with very high enantioselectivities. The catalyst is based on a previously reported design (J. Am. Chem. Soc. 2017, 139, 4322), in which iron(II) is surrounded by two configurationally inert achiral bidentate N-(2-pyridyl)-substituted N-heterocyclic carbenes in a C2-symmetric fashion and complemented by two labile acetonitriles. By replacing mesityl with more bulky 2,6-diisopropylphenyl substituents at the NHC ligands, the steric hindrance at the catalytic site was increased, thereby providing a markedly improved asymmetric induction. The new chiral-at-iron catalyst was applied to the inverse electron demand hetero-Diels-Alder reaction between β,γ-unsaturated α-ketoester and enol ethers provide 3,4-dihydro-2H-pyrans in high yields with excellent diastereoselectivities (up to 99 : 1 dr) and excellent enantioselectivities (up to 98 % ee). Other electron rich dienophiles are also suitable as demonstrated for a reaction with a vinyl azide." @default.
- W3152966822 created "2021-04-26" @default.
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- W3152966822 date "2021-05-07" @default.
- W3152966822 modified "2023-10-16" @default.
- W3152966822 title "Chiral‐at‐Iron Catalyst for Highly Enantioselective and Diastereoselective Hetero‐Diels‐Alder Reaction" @default.
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- W3152966822 doi "https://doi.org/10.1002/chem.202100703" @default.
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