CaCl2, Bisoxazoline, and Malonate: A Protocol for an Asymmetric Michael Reaction

Kristin Lippur; Sandra Kaabel; Ivar Järving; Kari Rissanen; Tõnis Kanger

doi:10.1021/acs.joc.5b00769

CaCl₂, Bisoxazoline, and Malonate: A Protocol for an Asymmetric Michael Reaction

Kristin Lippur, Sandra Kaabel, Ivar Järving, Kari Rissanen, Tõnis Kanger^*

^*Corresponding author for this work

Not published at Aalto University

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

25 Citations (Scopus)

Abstract

A mild protocol for the asymmetric Michael addition of dimethyl malonate to various α,β-unsaturated carbonyl compounds was developed. The salient feature of this methodology is that a cheap and environmentally friendly Lewis acid, CaCl₂, was used as a catalyst. An aminoindanol- and pyridine-derived ligand provided in the presence of CaCl₂ Michael adducts in moderate to high enantioselectivities. The scope of the reaction was demonstrated.

Original language	English
Pages (from-to)	6336-6341
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	80
Issue number	12
DOIs	https://doi.org/10.1021/acs.joc.5b00769
Publication status	Published - 19 Jun 2015
MoE publication type	A1 Journal article-refereed

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abstract = "A mild protocol for the asymmetric Michael addition of dimethyl malonate to various α,β-unsaturated carbonyl compounds was developed. The salient feature of this methodology is that a cheap and environmentally friendly Lewis acid, CaCl2, was used as a catalyst. An aminoindanol- and pyridine-derived ligand provided in the presence of CaCl2 Michael adducts in moderate to high enantioselectivities. The scope of the reaction was demonstrated.",

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AU - Lippur, Kristin

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AU - Rissanen, Kari

AU - Kanger, Tõnis

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AB - A mild protocol for the asymmetric Michael addition of dimethyl malonate to various α,β-unsaturated carbonyl compounds was developed. The salient feature of this methodology is that a cheap and environmentally friendly Lewis acid, CaCl2, was used as a catalyst. An aminoindanol- and pyridine-derived ligand provided in the presence of CaCl2 Michael adducts in moderate to high enantioselectivities. The scope of the reaction was demonstrated.

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CaCl₂, Bisoxazoline, and Malonate: A Protocol for an Asymmetric Michael Reaction

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