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1 article(s) from Kim, Doyoon

Recent advances in allylation of chiral secondary alkylcopper species

Minjae Kim,
Gwanggyun Kim,
Doyoon Kim,
Jun Hee Lee and
Seung Hwan Cho

Beilstein J. Org. Chem. 2025, 21, 639–658, doi:10.3762/bjoc.21.51

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Graphical Abstract

Scheme 1: Representative transition-metal catalysis for allylic substitution.

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Scheme 2: Formation of stereogenic centers in copper-catalyzed allylic alkylation reactions.

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Scheme 3: Copper-mediated, stereospecific S_N2-selective allylic substitution through retentive transmetalatio...

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Scheme 4: ZnCl₂-promoted stereospecific S_N2' allylic substitution of secondary alkylcopper species via sequen...

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Scheme 5: Temperature and time-dependent configurational stability of chiral secondary organocopper species.

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Scheme 6: DFT analysis of B–C bond lengths in various boronate complexes and correlation with reactivity.

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Scheme 7: Copper-catalyzed stereospecific allylic alkylation of secondary alkylboronic esters via tert-butyll...

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Scheme 8: Copper-catalyzed stereospecific allylic alkylation of chiral tertiary alkylboronic esters via adama...

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Scheme 9: DFT-calculated energy surface for boron-to-copper transmetalation of either the tert-butyl group or...

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Scheme 10: CuH-catalyzed enantioselective allylic substitution and postulated catalytic cycle.

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Scheme 11: CuH-catalyzed enantioselective allylic substitution of vinylarenes.

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Scheme 12: CuH-catalyzed stereoselective allylic substitution of vinylboronic esters.

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Scheme 13: (a) Generation of chiral copper species via enantioselective CuH addition to vinylBpin. (b) Regardi...

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Scheme 14: CuH-catalyzed enantioselective allylic substitution of 1‐trifluoromethylalkenes with 18-crown-6.

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Scheme 15: CuH-catalyzed enantioselective allylic substitution of terminal alkynes.

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Scheme 16: Copper-catalyzed enantiotopic-group-selective allylic substitution of 1,1-diborylalkanes.

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Scheme 17: (a) Computational and (b) experimental studies to elucidate the mechanistic details of the enantiot...

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Scheme 18: Copper-catalyzed regio-, diastereo- and enantioselective allylic substitution of 1,1-diborylalkanes....

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Scheme 19: (a) Experimental and (b) computational studies to understand the stereoselectivities in oxidative a...

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Review

Published 20 Mar 2025

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