Diastereoselective Ti-mediated preparation of bicyclic aminocyclopropanes from N-alkenyl amides

Claire Madelaine; Andrea K. Buzas; Justyna A. Kowalska-Six; Yvan Six; Benoît Crousse

doi:10.1016/j.tetlet.2009.07.031

Diastereoselective Ti-mediated preparation of bicyclic aminocyclopropanes from N-alkenyl amides

Claire Madelaine
, Andrea K. Buzas
, Justyna A. Kowalska-Six
, Yvan Six
, Benoît Crousse

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

Abstract

Intramolecular Ti-mediated alkene-amide couplings of a range of N-alk-3-enyl amides fitted with a substituent at the homoallylic position are described. CF₃-substituted compounds are suitable substrates and bicyclic aminocyclopropanes bearing a CF₃ group can be prepared in this way. Good diastereoselectivities can be observed depending on the substitution pattern, and best results are obtained in diethyl ether rather than in THF.

Original language	English
Pages (from-to)	5367-5371
Number of pages	5
Journal	Tetrahedron Letters
Volume	50
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2009.07.031
Publication status	Published - 23 Sept 2009
Externally published	Yes

Keywords

Cyclopropanes
Fluorine-substituted compounds
Kulinkovich-de Meijere reaction
Titanium

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10.1016/j.tetlet.2009.07.031

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title = "Diastereoselective Ti-mediated preparation of bicyclic aminocyclopropanes from N-alkenyl amides",

abstract = "Intramolecular Ti-mediated alkene-amide couplings of a range of N-alk-3-enyl amides fitted with a substituent at the homoallylic position are described. CF3-substituted compounds are suitable substrates and bicyclic aminocyclopropanes bearing a CF3 group can be prepared in this way. Good diastereoselectivities can be observed depending on the substitution pattern, and best results are obtained in diethyl ether rather than in THF.",

keywords = "Cyclopropanes, Fluorine-substituted compounds, Kulinkovich-de Meijere reaction, Titanium",

author = "Claire Madelaine and Buzas, \{Andrea K.\} and Kowalska-Six, \{Justyna A.\} and Yvan Six and Beno{\^i}t Crousse",

year = "2009",

month = sep,

day = "23",

doi = "10.1016/j.tetlet.2009.07.031",

language = "English",

volume = "50",

pages = "5367--5371",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "38",

}

TY - JOUR

T1 - Diastereoselective Ti-mediated preparation of bicyclic aminocyclopropanes from N-alkenyl amides

AU - Madelaine, Claire

AU - Buzas, Andrea K.

AU - Kowalska-Six, Justyna A.

AU - Six, Yvan

AU - Crousse, Benoît

PY - 2009/9/23

Y1 - 2009/9/23

N2 - Intramolecular Ti-mediated alkene-amide couplings of a range of N-alk-3-enyl amides fitted with a substituent at the homoallylic position are described. CF3-substituted compounds are suitable substrates and bicyclic aminocyclopropanes bearing a CF3 group can be prepared in this way. Good diastereoselectivities can be observed depending on the substitution pattern, and best results are obtained in diethyl ether rather than in THF.

AB - Intramolecular Ti-mediated alkene-amide couplings of a range of N-alk-3-enyl amides fitted with a substituent at the homoallylic position are described. CF3-substituted compounds are suitable substrates and bicyclic aminocyclopropanes bearing a CF3 group can be prepared in this way. Good diastereoselectivities can be observed depending on the substitution pattern, and best results are obtained in diethyl ether rather than in THF.

KW - Cyclopropanes

KW - Fluorine-substituted compounds

KW - Kulinkovich-de Meijere reaction

KW - Titanium

U2 - 10.1016/j.tetlet.2009.07.031

DO - 10.1016/j.tetlet.2009.07.031

M3 - Article

AN - SCOPUS:68049124581

SN - 0040-4039

VL - 50

SP - 5367

EP - 5371

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

Diastereoselective Ti-mediated preparation of bicyclic aminocyclopropanes from N-alkenyl amides

Abstract

Keywords

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