Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers

Ilyas A. Berhane; Ameya S. Burde; Jonathan J. Kennedy-Ellis; Eva Zurek; Sherry R. Chemler

doi:10.1039/d1cc03515k

Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers

Ilyas A. Berhane
, Ameya S. Burde
, Jonathan J. Kennedy-Ellis
, Eva Zurek
, Sherry R. Chemler

Chemistry

SUNY Buffalo

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

12 Scopus citations

Abstract

The enantioselective copper-catalyzed oxidative coupling of alkenols with styrenes for the construction of dihydropyrans, isochromans, pyrans and morpholines is reported. A concise formal synthesis of a σ₁receptor ligand using this alkene carboetherification methodology was demonstrated. Ligand, solvent and base all impact reaction efficiency. DFT transition state calculations are presented.

Original language	English
Pages (from-to)	10099-10102
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	78
DOIs	https://doi.org/10.1039/d1cc03515k
State	Published - Oct 7 2021

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title = "Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers",

abstract = "The enantioselective copper-catalyzed oxidative coupling of alkenols with styrenes for the construction of dihydropyrans, isochromans, pyrans and morpholines is reported. A concise formal synthesis of a σ1receptor ligand using this alkene carboetherification methodology was demonstrated. Ligand, solvent and base all impact reaction efficiency. DFT transition state calculations are presented.",

author = "Berhane, \{Ilyas A.\} and Burde, \{Ameya S.\} and Kennedy-Ellis, \{Jonathan J.\} and Eva Zurek and Chemler, \{Sherry R.\}",

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T1 - Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers

AU - Berhane, Ilyas A.

AU - Burde, Ameya S.

AU - Kennedy-Ellis, Jonathan J.

AU - Zurek, Eva

AU - Chemler, Sherry R.

N1 - Publisher Copyright: © The Royal Society of Chemistry 2021.

PY - 2021/10/7

Y1 - 2021/10/7

N2 - The enantioselective copper-catalyzed oxidative coupling of alkenols with styrenes for the construction of dihydropyrans, isochromans, pyrans and morpholines is reported. A concise formal synthesis of a σ1receptor ligand using this alkene carboetherification methodology was demonstrated. Ligand, solvent and base all impact reaction efficiency. DFT transition state calculations are presented.

AB - The enantioselective copper-catalyzed oxidative coupling of alkenols with styrenes for the construction of dihydropyrans, isochromans, pyrans and morpholines is reported. A concise formal synthesis of a σ1receptor ligand using this alkene carboetherification methodology was demonstrated. Ligand, solvent and base all impact reaction efficiency. DFT transition state calculations are presented.

UR - https://www.scopus.com/pages/publications/85116306581

U2 - 10.1039/d1cc03515k

DO - 10.1039/d1cc03515k

M3 - Article

C2 - 34518847

AN - SCOPUS:85116306581

SN - 1359-7345

VL - 57

SP - 10099

EP - 10102

JO - Chemical Communications

JF - Chemical Communications

IS - 78

ER -

Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers

Abstract

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