Synthesis of Highly Enantioenriched All-Carbon Quaternary Centers: Conjugate Additions of Chiral Organolithium Nucleophiles to α,α- Dinitrile β,β-Disubstituted Olefins

Doo Ok Jang; Dwight D. Kim; Do Kyu Pyun; Peter Beak

doi:10.1021/ol035601k

Synthesis of Highly Enantioenriched All-Carbon Quaternary Centers: Conjugate Additions of Chiral Organolithium Nucleophiles to α,α- Dinitrile β,β-Disubstituted Olefins

Doo Ok Jang, Dwight D. Kim, Do Kyu Pyun, Peter Beak

Chemistry and Medical Chemistry

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

5 Citations (Scopus)

Abstract

(Equation presented) Highly enantioenriched quaternary centers are obtained by the reaction of chiral lithiated intermediates complexed to (-)-sparteine with tetrasubstituted, α,α-dinitrile activated olefins. Lithiated N-Boc-N-Aryl benzylamine furnishes products with drs from 78:22 to 95:5, with ers exceeding 94:6. Lithiated N-Boc-N-Aryl allylamine reactants provide enecarbamate products with drs from 55:45 to 99:1, with ers ranging from 87:13 to 97:3.

Original language	English
Pages (from-to)	4155-4157
Number of pages	3
Journal	Organic Letters
Volume	5
Issue number	22
DOIs	https://doi.org/10.1021/ol035601k
Publication status	Published - 2003 Oct 30

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis of Highly Enantioenriched All-Carbon Quaternary Centers: Conjugate Additions of Chiral Organolithium Nucleophiles to α,α- Dinitrile β,β-Disubstituted Olefins",

abstract = "(Equation presented) Highly enantioenriched quaternary centers are obtained by the reaction of chiral lithiated intermediates complexed to (-)-sparteine with tetrasubstituted, α,α-dinitrile activated olefins. Lithiated N-Boc-N-Aryl benzylamine furnishes products with drs from 78:22 to 95:5, with ers exceeding 94:6. Lithiated N-Boc-N-Aryl allylamine reactants provide enecarbamate products with drs from 55:45 to 99:1, with ers ranging from 87:13 to 97:3.",

author = "Jang, {Doo Ok} and Kim, {Dwight D.} and Pyun, {Do Kyu} and Peter Beak",

year = "2003",

month = oct,

day = "30",

doi = "10.1021/ol035601k",

language = "English",

volume = "5",

pages = "4155--4157",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "22",

}

TY - JOUR

T1 - Synthesis of Highly Enantioenriched All-Carbon Quaternary Centers

T2 - Conjugate Additions of Chiral Organolithium Nucleophiles to α,α- Dinitrile β,β-Disubstituted Olefins

AU - Jang, Doo Ok

AU - Kim, Dwight D.

AU - Pyun, Do Kyu

AU - Beak, Peter

PY - 2003/10/30

Y1 - 2003/10/30

N2 - (Equation presented) Highly enantioenriched quaternary centers are obtained by the reaction of chiral lithiated intermediates complexed to (-)-sparteine with tetrasubstituted, α,α-dinitrile activated olefins. Lithiated N-Boc-N-Aryl benzylamine furnishes products with drs from 78:22 to 95:5, with ers exceeding 94:6. Lithiated N-Boc-N-Aryl allylamine reactants provide enecarbamate products with drs from 55:45 to 99:1, with ers ranging from 87:13 to 97:3.

AB - (Equation presented) Highly enantioenriched quaternary centers are obtained by the reaction of chiral lithiated intermediates complexed to (-)-sparteine with tetrasubstituted, α,α-dinitrile activated olefins. Lithiated N-Boc-N-Aryl benzylamine furnishes products with drs from 78:22 to 95:5, with ers exceeding 94:6. Lithiated N-Boc-N-Aryl allylamine reactants provide enecarbamate products with drs from 55:45 to 99:1, with ers ranging from 87:13 to 97:3.

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U2 - 10.1021/ol035601k

DO - 10.1021/ol035601k

M3 - Article

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AN - SCOPUS:0344082878

SN - 1523-7060

VL - 5

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JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Synthesis of Highly Enantioenriched All-Carbon Quaternary Centers: Conjugate Additions of Chiral Organolithium Nucleophiles to α,α- Dinitrile β,β-Disubstituted Olefins

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