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4 article(s) from Marek, Ilan

Diastereo- and enantioselective preparation of cyclopropanol derivatives

Marwan Simaan and
Ilan Marek

Beilstein J. Org. Chem. 2019, 15, 752–760, doi:10.3762/bjoc.15.71

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Scheme 1: Various strategies leading to the formation of cyclopropanols.

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Scheme 2: General approach to the preparation of cyclopropanol and cyclopropylamine derivatives.

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Figure 1: Prerequisite for a regio- and diastereoselective carbometalation.

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Scheme 3: Preparation of cyclopropenyl methyl ethers 3a–d.

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Scheme 4: Regio- and diastereoselective carbocupration of cyclopropenyl methyl ethers 3a,c.

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Scheme 5: Diastereoselective formation of cyclopropanols.

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Scheme 6: Diastereoselective carbometalation/oxidation of nonfunctionalized cyclopropenes 6.

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Scheme 7: Preparation of diastereoisomerically pure and enantioenriched cyclopropanols and cyclopropylamines.

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Published 21 Mar 2019

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Regio- and stereoselective carbometallation reactions of N-alkynylamides and sulfonamides

Yury Minko,
Morgane Pasco,
Helena Chechik and
Ilan Marek

Beilstein J. Org. Chem. 2013, 9, 526–532, doi:10.3762/bjoc.9.57

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Scheme 1: Possible regioisomers obtained in the carbocupration reaction of α-heterosubstituted acetylenes 1.

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Scheme 2: Regioselective carbometallation of N-alkynylsulfonamide 2.

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Scheme 3: Regioselective carbometallation of ynamide 4.

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Scheme 4: Regioselective carbometallation of cyclic N-alkynylcarbamate 7.

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Figure 1: Molecular structure of 9f (hydrogen atoms except of H9 and H10 are omitted for clarity).

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Published 13 Mar 2013

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Carbometallation chemistry

Ilan Marek

Beilstein J. Org. Chem. 2013, 9, 234–235, doi:10.3762/bjoc.9.27

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Editorial

Published 04 Feb 2013

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Recent advances in carbocupration of α-heterosubstituted alkynes

Ahmad Basheer and
Ilan Marek

Beilstein J. Org. Chem. 2010, 6, No. 77, doi:10.3762/bjoc.6.77

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Scheme 1: General scheme for the carbocupration reaction.

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Scheme 2: Regioselectivity in the carbocupration reaction.

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Scheme 3: Carbocupration of α-alkoxyalkynes.

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Scheme 4: Carbocupration of substituted α-alkoxyalkynes.

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Scheme 5: Formation of the branched isomer.

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Scheme 6: Formation of the linear isomer.

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Scheme 7: Carbocupration of O-alkynyl carbamates.

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Scheme 8: Carbocupration of ynamines.

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Scheme 9: Carbocupration of ynamide.

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Scheme 10: Formation of aldol products possessing stereogenic quaternary carbon centers.

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Scheme 11: Carbocupration of alkynyl sulfonamide.

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Scheme 12: Tandem carbocupration-sigmatropic rearrangement.

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Scheme 13: Silylcupration of alkynyl sulfonamides.

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Scheme 14: Carbocupration of P-substituted alkynes.

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Scheme 15: Carbocupration of alkynylphosphonates.

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Scheme 16: Carbocupration of thioalkynes.

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Scheme 17: Tandem carbocupration-1,2-metalate rearrangement.

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Scheme 18: Carbocupration with functionalized organocopper species.

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Scheme 19: Carbocupration of alkynyl sulfoxides.

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Scheme 20: Carbocupration of alkynyl sulfones.

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Scheme 21: Carbocupration of alkynyl sulfoximines.

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Scheme 22: Carbocupration of alkynylsilanes.

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Scheme 23: Carbocupration of functionalized alkynylsilanes.

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Scheme 24: Silyl- and stannyl cupration of silyl- and stannylalkynes.

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Review

Published 15 Jul 2010

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