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

20 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

Access to Document

10.1039/c4ob02601b

Cite this

@article{74cdd0d1cd7642d6a200363ef319af35,

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.",

author = "Targel, {Tom A.} and Kumar, {Jayprakash N.} and Shneider, {O. Svetlana} and Sukanta Bar and Natalia Fridman and Shimon Maximenko and Szpilman, {Alex M.}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2015.",

year = "2015",

month = mar,

day = "7",

doi = "10.1039/c4ob02601b",

language = "אנגלית",

volume = "13",

pages = "2546--2549",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "9",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=84923379313&partnerID=8YFLogxK

U2 - 10.1039/c4ob02601b

DO - 10.1039/c4ob02601b

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:84923379313

SN - 1477-0520

VL - 13

SP - 2546

EP - 2549

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 9

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this