Ligand-controlled iron-catalyzed coupling of α-substituted β-ketoesters with phenols

Regev Parnes; Umesh A. Kshirsagar; Aviya Werbeloff; Clil Regev; Doron Pappo

doi:https://doi.org/10.1021/ol301297k

Ligand-controlled iron-catalyzed coupling of α-substituted β-ketoesters with phenols

Regev Parnes, Umesh A. Kshirsagar, Aviya Werbeloff, Clil Regev, Doron Pappo

Ben-Gurion University of the Negev

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

Abstract

A chemo-, regio-, and stereoselective FeCl ₃/1,10-phenanthroline- catalyzed cross dehydrogenative coupling (CDC) reaction between phenols and α-substituted β-ketoesters was developed. The reaction creates a new quaternary carbon center within a polycyclic hemiacetal or polycyclic spirolactone architecture. The applicability of the new method to the synthesis of natural products was demonstrated by a possible biomimetic synthesis of the lachnanthospirone core.

Original language	American English
Pages (from-to)	3324-3327
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	13
DOIs	https://doi.org/10.1021/ol301297k
State	Published - 6 Jul 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Ligand-controlled iron-catalyzed coupling of α-substituted β-ketoesters with phenols",

abstract = "A chemo-, regio-, and stereoselective FeCl 3/1,10-phenanthroline- catalyzed cross dehydrogenative coupling (CDC) reaction between phenols and α-substituted β-ketoesters was developed. The reaction creates a new quaternary carbon center within a polycyclic hemiacetal or polycyclic spirolactone architecture. The applicability of the new method to the synthesis of natural products was demonstrated by a possible biomimetic synthesis of the lachnanthospirone core.",

author = "Regev Parnes and Kshirsagar, {Umesh A.} and Aviya Werbeloff and Clil Regev and Doron Pappo",

year = "2012",

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doi = "https://doi.org/10.1021/ol301297k",

language = "American English",

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AU - Parnes, Regev

AU - Kshirsagar, Umesh A.

AU - Werbeloff, Aviya

AU - Regev, Clil

AU - Pappo, Doron

PY - 2012/7/6

Y1 - 2012/7/6

N2 - A chemo-, regio-, and stereoselective FeCl 3/1,10-phenanthroline- catalyzed cross dehydrogenative coupling (CDC) reaction between phenols and α-substituted β-ketoesters was developed. The reaction creates a new quaternary carbon center within a polycyclic hemiacetal or polycyclic spirolactone architecture. The applicability of the new method to the synthesis of natural products was demonstrated by a possible biomimetic synthesis of the lachnanthospirone core.

AB - A chemo-, regio-, and stereoselective FeCl 3/1,10-phenanthroline- catalyzed cross dehydrogenative coupling (CDC) reaction between phenols and α-substituted β-ketoesters was developed. The reaction creates a new quaternary carbon center within a polycyclic hemiacetal or polycyclic spirolactone architecture. The applicability of the new method to the synthesis of natural products was demonstrated by a possible biomimetic synthesis of the lachnanthospirone core.

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U2 - https://doi.org/10.1021/ol301297k

DO - https://doi.org/10.1021/ol301297k

M3 - Article

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VL - 14

SP - 3324

EP - 3327

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Ligand-controlled iron-catalyzed coupling of α-substituted β-ketoesters with phenols

Abstract

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