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

פרסום מחקרי: פרסום בכתב עת › מאמר › ביקורת עמיתים

24 ציטוטים ‏(Scopus)

תקציר

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.

שפה מקורית	אנגלית
עמודים (מ-עד)	2546-2549
מספר עמודים	4
כתב עת	Organic and Biomolecular Chemistry
כרך	13
מספר גיליון	9
מזהי עצם דיגיטלי (DOIs)	https://doi.org/10.1039/c4ob02601b
סטטוס פרסום	פורסם - 7 מרץ 2015
פורסם באופן חיצוני	כן

גישה למסמך

10.1039/c4ob02601b

קבצים וקישורים אחרים

Link to publication in Scopus

פורמט ציטוט ביבליוגרפי

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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.",

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 - https://www.scopus.com/pages/publications/84923379313

U2 - 10.1039/c4ob02601b

DO - 10.1039/c4ob02601b

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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

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