Amino Imidate-Catalyzed Asymmetric Michael Reactions of Ketones and Nitroalkenes

Paul Andrew Clarke; Bohdan Sosunovych; Alexander Brown

doi:10.1055/a-1761-4495

Amino Imidate-Catalyzed Asymmetric Michael Reactions of Ketones and Nitroalkenes

Paul Andrew Clarke, Bohdan Sosunovych, Alexander Brown

Chemistry

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

Abstract

The efficiency of an amino imidate organocatalyst was evaluated in the Michael reaction of ketones with nitroalkenes. tert-Butyl L-proline imidate was found to be a syn-selective catalyst generating products with moderate to good enantioselectivities, of up to 84% e.e. The best substrates were found to be cyclic ketones and -nitrostyrenes. The catalytic efficiency and enantioselectivity was enhanced by the addition of 10 mol% of benzoic acid.

Original language	English
Article number	SO-2022-01-0005-OP.R1
Pages (from-to)	67-74
Number of pages	8
Journal	SynOpen
Volume	6
Early online date	4 Feb 2022
DOIs	https://doi.org/10.1055/a-1761-4495
Publication status	Published - 24 Feb 2022

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10.1055/a-1761-4495Licence: CC BY-NC-ND

a-1761-4495Accepted author manuscript, 3.43 MBLicence: CC BY-NC-ND

1 Finished

Investigating the use of Amino nitriles and Amino imidates as organocatalysts
Clarke, P. A. (Principal investigator), Vagkidis, N. (Student) & Sosunovych, B. (Student)
1/10/17 → 30/04/22
Project: Other project › Miscellaneous project

Aminoimidate Catalysed Michael Addition of Carbonyl Compounds to Nitroalkenes
Clarke, P. A. (Creator), Sosunovych, B. (Contributor) & Brown, A. (Contributor), University of York, 1 Oct 2021
DOI: 10.15124/207e9639-5f06-4eea-af9c-4ded13054afa
Dataset

Cite this

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title = "Amino Imidate-Catalyzed Asymmetric Michael Reactions of Ketones and Nitroalkenes",

abstract = "The efficiency of an amino imidate organocatalyst was evaluated in the Michael reaction of ketones with nitroalkenes. tert-Butyl L-proline imidate was found to be a syn-selective catalyst generating products with moderate to good enantioselectivities, of up to 84% e.e. The best substrates were found to be cyclic ketones and -nitrostyrenes. The catalytic efficiency and enantioselectivity was enhanced by the addition of 10 mol% of benzoic acid.",

author = "Clarke, {Paul Andrew} and Bohdan Sosunovych and Alexander Brown",

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N2 - The efficiency of an amino imidate organocatalyst was evaluated in the Michael reaction of ketones with nitroalkenes. tert-Butyl L-proline imidate was found to be a syn-selective catalyst generating products with moderate to good enantioselectivities, of up to 84% e.e. The best substrates were found to be cyclic ketones and -nitrostyrenes. The catalytic efficiency and enantioselectivity was enhanced by the addition of 10 mol% of benzoic acid.

AB - The efficiency of an amino imidate organocatalyst was evaluated in the Michael reaction of ketones with nitroalkenes. tert-Butyl L-proline imidate was found to be a syn-selective catalyst generating products with moderate to good enantioselectivities, of up to 84% e.e. The best substrates were found to be cyclic ketones and -nitrostyrenes. The catalytic efficiency and enantioselectivity was enhanced by the addition of 10 mol% of benzoic acid.

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DO - 10.1055/a-1761-4495

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JO - SynOpen

JF - SynOpen

M1 - SO-2022-01-0005-OP.R1

ER -

Amino Imidate-Catalyzed Asymmetric Michael Reactions of Ketones and Nitroalkenes

Abstract

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Projects

Investigating the use of Amino nitriles and Amino imidates as organocatalysts

Datasets

Aminoimidate Catalysed Michael Addition of Carbonyl Compounds to Nitroalkenes

Cite this