Stereoselective Sc(OTf)3-Catalyzed Aldol Reactions of Disubstituted Silyl Enol Ethers of Aldehydes with Acetals

Peter Yong Wang; Itai Massad; Ilan Marek

doi:10.1002/anie.202101634

Stereoselective Sc(OTf)₃-Catalyzed Aldol Reactions of Disubstituted Silyl Enol Ethers of Aldehydes with Acetals

Peter Yong Wang, Itai Massad, Ilan Marek

Technion - Israel Institute of Technology

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

Abstract

Facile and modular access to stereodefined disubstituted aldehyde-derived silyl enol ethers allowed their successful application in a stereoselective aldol reaction affording the products with excellent yields and diastereomeric ratios. The counter-intuitive stereochemical behavior of this Mukaiyama-aldol reaction is accounted for by a non-classical open transition state.

Original language	English
Pages (from-to)	12765-12769
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	23
DOIs	https://doi.org/10.1002/anie.202101634
State	Published - 1 Jun 2021

Keywords

Mukaiyama-aldol reaction
acetals
enolates
scandium
selectivity

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

Access to Document

10.1002/anie.202101634

Cite this

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title = "Stereoselective Sc(OTf)3-Catalyzed Aldol Reactions of Disubstituted Silyl Enol Ethers of Aldehydes with Acetals",

abstract = "Facile and modular access to stereodefined disubstituted aldehyde-derived silyl enol ethers allowed their successful application in a stereoselective aldol reaction affording the products with excellent yields and diastereomeric ratios. The counter-intuitive stereochemical behavior of this Mukaiyama-aldol reaction is accounted for by a non-classical open transition state.",

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AU - Massad, Itai

AU - Marek, Ilan

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AB - Facile and modular access to stereodefined disubstituted aldehyde-derived silyl enol ethers allowed their successful application in a stereoselective aldol reaction affording the products with excellent yields and diastereomeric ratios. The counter-intuitive stereochemical behavior of this Mukaiyama-aldol reaction is accounted for by a non-classical open transition state.

KW - Mukaiyama-aldol reaction

KW - acetals

KW - enolates

KW - scandium

KW - selectivity

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M3 - مقالة

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