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

Martin Kamlar; Natalia Bravo; Andrea Nekane R. Alba; Simona Hybelbauerová; Ivana Císařová; Jan Veselý; Albert Moyano; Ramon Rios

doi:10.1002/ejoc.201000851

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

Martin Kamlar, Natalia Bravo, Andrea Nekane R. Alba, Simona Hybelbauerová, Ivana Císařová, Jan Veselý, Albert Moyano, Ramon Rios

Chemistry

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

33 Scopus citations

Abstract

An organocatalytic, highly enantioselective addition of 1fluoro-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.

Original language	British English
Pages (from-to)	5464-5470
Number of pages	7
Journal	European Journal of Organic Chemistry
Issue number	28
DOIs	https://doi.org/10.1002/ejoc.201000851
State	Published - Oct 2010

Keywords

Aldehydes
Diastereoselectivity
Enantioselectivity
Fluorine
Michael addition
Organocatalysis

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10.1002/ejoc.201000851

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

abstract = "An organocatalytic, highly enantioselective addition of 1fluoro-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.",

keywords = "Aldehydes, Diastereoselectivity, Enantioselectivity, Fluorine, Michael addition, Organocatalysis",

author = "Martin Kamlar and Natalia Bravo and Alba, {Andrea Nekane R.} and Simona Hybelbauerov{\'a} and Ivana C{\'i}sa{\v r}ov{\'a} and Jan Vesel{\'y} and Albert Moyano and Ramon Rios",

year = "2010",

month = oct,

doi = "10.1002/ejoc.201000851",

language = "British English",

pages = "5464--5470",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - Highly enantioselective addition of 1-fluoro-1-nitro(phenylsulfonyl)methane to α,β-unsaturated aldehydes

AU - Kamlar, Martin

AU - Bravo, Natalia

AU - Alba, Andrea Nekane R.

AU - Hybelbauerová, Simona

AU - Císařová, Ivana

AU - Veselý, Jan

AU - Moyano, Albert

AU - Rios, Ramon

PY - 2010/10

Y1 - 2010/10

N2 - An organocatalytic, highly enantioselective addition of 1fluoro-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.

AB - An organocatalytic, highly enantioselective addition of 1fluoro-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.

KW - Aldehydes

KW - Diastereoselectivity

KW - Enantioselectivity

KW - Fluorine

KW - Michael addition

KW - Organocatalysis

UR - http://www.scopus.com/inward/record.url?scp=77957168849&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201000851

DO - 10.1002/ejoc.201000851

M3 - Article

AN - SCOPUS:77957168849

SN - 1434-193X

SP - 5464

EP - 5470

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 28

ER -

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

Abstract

Keywords

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