Oxidative asymmetric umpolung alkylation of Evans' β-ketoimides using dialkylzinc nucleophiles

Tom A. Targel; Jayprakash N. Kumar; O. Svetlana Shneider; Sukanta Bar; Natalia Fridman; Shimon Maximenko; Alex M. Szpilman

doi:10.1039/c4ob02601b

Oxidative asymmetric umpolung alkylation of Evans' β-ketoimides using dialkylzinc nucleophiles

Tom A. Targel, Jayprakash N. Kumar, O. Svetlana Shneider, Sukanta Bar, Natalia Fridman, Shimon Maximenko, Alex M. Szpilman

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

Abstract

Umpolung alkylation of Evans' auxiliary substituted β-ketoimides affords the diastereomerically pure products in yields ranging from 40 to 80%. The reaction itself proceeds with diastereoselectivities between 3:1 and 18:1. Dialkylzinc serves as the nucleophile and umpolung of the β-keto-imide enolate is achieved by the action of Koser's reagent.

Original language	English
Pages (from-to)	2546-2549
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	9
DOIs	https://doi.org/10.1039/c4ob02601b
State	Published - 7 Mar 2015
Externally published	Yes

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title = "Oxidative asymmetric umpolung alkylation of Evans' β-ketoimides using dialkylzinc nucleophiles",

abstract = "Umpolung alkylation of Evans' auxiliary substituted β-ketoimides affords the diastereomerically pure products in yields ranging from 40 to 80\%. The reaction itself proceeds with diastereoselectivities between 3:1 and 18:1. Dialkylzinc serves as the nucleophile and umpolung of the β-keto-imide enolate is achieved by the action of Koser's reagent.",

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doi = "10.1039/c4ob02601b",

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T1 - Oxidative asymmetric umpolung alkylation of Evans' β-ketoimides using dialkylzinc nucleophiles

AU - Targel, Tom A.

AU - Kumar, Jayprakash N.

AU - Shneider, O. Svetlana

AU - Bar, Sukanta

AU - Fridman, Natalia

AU - Maximenko, Shimon

AU - Szpilman, Alex M.

PY - 2015/3/7

Y1 - 2015/3/7

N2 - Umpolung alkylation of Evans' auxiliary substituted β-ketoimides affords the diastereomerically pure products in yields ranging from 40 to 80%. The reaction itself proceeds with diastereoselectivities between 3:1 and 18:1. Dialkylzinc serves as the nucleophile and umpolung of the β-keto-imide enolate is achieved by the action of Koser's reagent.

AB - Umpolung alkylation of Evans' auxiliary substituted β-ketoimides affords the diastereomerically pure products in yields ranging from 40 to 80%. The reaction itself proceeds with diastereoselectivities between 3:1 and 18:1. Dialkylzinc serves as the nucleophile and umpolung of the β-keto-imide enolate is achieved by the action of Koser's reagent.

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U2 - 10.1039/c4ob02601b

DO - 10.1039/c4ob02601b

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AN - SCOPUS:84923379313

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 9

ER -

Oxidative asymmetric umpolung alkylation of Evans' β-ketoimides using dialkylzinc nucleophiles

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