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Highly enantioselective addition of 1-fluoro-1-nitro(phenylsulfonyl)methane to α,β-unsaturated aldehydes

Highly enantioselective addition of 1-fluoro-1-nitro(phenylsulfonyl)methane to α,β-unsaturated aldehydes
Highly enantioselective addition of 1-fluoro-1-nitro(phenylsulfonyl)methane to α,β-unsaturated aldehydes
An organocatalytic, highly enantioselective addition of 1-fluoro-1-nitro(phenylsulfonyl)methane to α,β-unsaturated aldehydes is reported. The reaction is simply catalyzed by secondary amines and furnishes the corresponding fluorinated derivatives in good yields, with moderate diastereoselectivities and excellent enantioselectivities. The absolute configuration of the major diastereomers was unambiguously ascertained by X-ray diffraction analysis.
fluorine, organocatalysis, aldehydes, enantioselectivity, diastereoselectivity, michael addition
1434-193X
5464-5470
Kamlar, Martin
4cb85f32-9d4a-4beb-9b8a-db0e8e1f0ab0
Bravo, Natalia
b4885173-6065-4fb7-accb-392f7d05735b
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Hybelbauerová, Simona
812c9cdf-50f5-4b78-bc3f-071f4bbab204
Císařová, Ivana
a77909ed-89d0-4f6d-90a1-2b2ab196870d
Veselý, Jan
9d4ecc53-859e-451a-a018-636d416bb3fe
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Kamlar, Martin
4cb85f32-9d4a-4beb-9b8a-db0e8e1f0ab0
Bravo, Natalia
b4885173-6065-4fb7-accb-392f7d05735b
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Hybelbauerová, Simona
812c9cdf-50f5-4b78-bc3f-071f4bbab204
Císařová, Ivana
a77909ed-89d0-4f6d-90a1-2b2ab196870d
Veselý, Jan
9d4ecc53-859e-451a-a018-636d416bb3fe
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Kamlar, Martin, Bravo, Natalia, Alba, Andrea-Nekane R., Hybelbauerová, Simona, Císařová, Ivana, Veselý, Jan, Moyano, Albert and Rios, Ramon (2010) Highly enantioselective addition of 1-fluoro-1-nitro(phenylsulfonyl)methane to α,β-unsaturated aldehydes. European Journal of Organic Chemistry, 2010 (28), 5464-5470. (doi:10.1002/ejoc.201000851).

Record type: Article

Abstract

An organocatalytic, highly enantioselective addition of 1-fluoro-1-nitro(phenylsulfonyl)methane to α,β-unsaturated aldehydes is reported. The reaction is simply catalyzed by secondary amines and furnishes the corresponding fluorinated derivatives in good yields, with moderate diastereoselectivities and excellent enantioselectivities. The absolute configuration of the major diastereomers was unambiguously ascertained by X-ray diffraction analysis.

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More information

e-pub ahead of print date: 16 August 2010
Published date: 2010
Keywords: fluorine, organocatalysis, aldehydes, enantioselectivity, diastereoselectivity, michael addition
Organisations: Chemistry

Identifiers

Local EPrints ID: 347703
URI: http://eprints.soton.ac.uk/id/eprint/347703
ISSN: 1434-193X
PURE UUID: c42e5cef-7ec0-4295-a111-4e439cdf8cba
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

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Date deposited: 29 Jan 2013 11:34
Last modified: 03 Dec 2019 01:38

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Contributors

Author: Martin Kamlar
Author: Natalia Bravo
Author: Andrea-Nekane R. Alba
Author: Simona Hybelbauerová
Author: Ivana Císařová
Author: Jan Veselý
Author: Albert Moyano
Author: Ramon Rios ORCID iD

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