Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides from Glycals

Carlos Palo-Nieto; Abhijit Sau; Robin Jeanneret; Pierre-Adrien Payard; Aude Salamé; Maristela Braga Martins-Teixeira; Ivone Carvalho; Laurence Grimaud; M Carmen Galan

doi:10.1021/acs.orglett.9b04525

Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides from Glycals

Carlos Palo-Nieto, Abhijit Sau, Robin Jeanneret, Pierre-Adrien Payard, Aude Salamé, Maristela Braga Martins-Teixeira, Ivone Carvalho, Laurence Grimaud, M Carmen Galan

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

28 Citations (Scopus)

Abstract

We demonstrate that tuning the reactivity of Cu by the choice of oxidation state and counterion leads to the activation of both "armed" and "disarmed" type glycals toward direct glycosylation leading to the α-stereoselective synthesis of deoxyglycosides in good to excellent yields. Mechanistic studies show that CuI is essential for effective catalysis and stereocontrol and that the reaction proceeds through dual activation of both the enol ether as well as the OH nucleophile.

Original language	English
Journal	Organic Letters
Volume	22
Issue number	5
Early online date	19 Feb 2020
DOIs	https://doi.org/10.1021/acs.orglett.9b04525
Publication status	Published - 6 Mar 2020

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title = "Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides from Glycals",

abstract = "We demonstrate that tuning the reactivity of Cu by the choice of oxidation state and counterion leads to the activation of both {"}armed{"} and {"}disarmed{"} type glycals toward direct glycosylation leading to the α-stereoselective synthesis of deoxyglycosides in good to excellent yields. Mechanistic studies show that CuI is essential for effective catalysis and stereocontrol and that the reaction proceeds through dual activation of both the enol ether as well as the OH nucleophile.",

author = "Carlos Palo-Nieto and Abhijit Sau and Robin Jeanneret and Pierre-Adrien Payard and Aude Salam{\'e} and Martins-Teixeira, {Maristela Braga} and Ivone Carvalho and Laurence Grimaud and Galan, {M Carmen}",

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doi = "10.1021/acs.orglett.9b04525",

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TY - JOUR

T1 - Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides from Glycals

AU - Palo-Nieto, Carlos

AU - Sau, Abhijit

AU - Jeanneret, Robin

AU - Payard, Pierre-Adrien

AU - Salamé, Aude

AU - Martins-Teixeira, Maristela Braga

AU - Carvalho, Ivone

AU - Grimaud, Laurence

AU - Galan, M Carmen

PY - 2020/3/6

Y1 - 2020/3/6

N2 - We demonstrate that tuning the reactivity of Cu by the choice of oxidation state and counterion leads to the activation of both "armed" and "disarmed" type glycals toward direct glycosylation leading to the α-stereoselective synthesis of deoxyglycosides in good to excellent yields. Mechanistic studies show that CuI is essential for effective catalysis and stereocontrol and that the reaction proceeds through dual activation of both the enol ether as well as the OH nucleophile.

AB - We demonstrate that tuning the reactivity of Cu by the choice of oxidation state and counterion leads to the activation of both "armed" and "disarmed" type glycals toward direct glycosylation leading to the α-stereoselective synthesis of deoxyglycosides in good to excellent yields. Mechanistic studies show that CuI is essential for effective catalysis and stereocontrol and that the reaction proceeds through dual activation of both the enol ether as well as the OH nucleophile.

U2 - 10.1021/acs.orglett.9b04525

DO - 10.1021/acs.orglett.9b04525

M3 - Article (Academic Journal)

C2 - 32073274

SN - 1523-7060

VL - 22

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Copper Reactivity Can Be Tuned to Catalyze the Stereoselective Synthesis of 2-Deoxyglycosides from Glycals

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