New aldehydes by catalytic diene cycloisomerisations

Fanny Grau; J. Carles Bayón; Pedro A. Aguirre; Teodor Parella; Elisabet Duñach

doi:10.1002/ejoc.200700881

New aldehydes by catalytic diene cycloisomerisations

Fanny Grau, J. Carles Bayón, Pedro A. Aguirre, Teodor Parella, Elisabet Duñach

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Abstract

The Rh-catalysed hydroformylation of isopropylidenecyclohexane derivatives obtained by intramolecular diene cyclisations affords the corresponding aldehydes in good yields and in a completely chemo- and regioselective manner. Diastereoselectivities of ca. 90%were achieved for all substrates when a bulky phosphite was used as the Rh ligand. The stereochemical outcomes of the hydroformylation reactions were established by detailed NMR studies. The olfactory evaluation of the different aldehydes is also presented. © Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Original language	English
Pages (from-to)	1214-1223
Journal	European Journal of Organic Chemistry
Issue number	7
DOIs	https://doi.org/10.1002/ejoc.200700881 https://doi.org/10.1002/ejoc.20070088
Publication status	Published - 1 Mar 2008

Keywords

Aldehydes
Hydroformylation
Isopropylidenecyclohexane
NMR spectroscopy
Stereochemistry

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title = "New aldehydes by catalytic diene cycloisomerisations",

abstract = "The Rh-catalysed hydroformylation of isopropylidenecyclohexane derivatives obtained by intramolecular diene cyclisations affords the corresponding aldehydes in good yields and in a completely chemo- and regioselective manner. Diastereoselectivities of ca. 90%were achieved for all substrates when a bulky phosphite was used as the Rh ligand. The stereochemical outcomes of the hydroformylation reactions were established by detailed NMR studies. The olfactory evaluation of the different aldehydes is also presented. {\textcopyright} Wiley-VCH Verlag GmbH & Co. KGaA, 2008.",

keywords = "Aldehydes, Hydroformylation, Isopropylidenecyclohexane, NMR spectroscopy, Stereochemistry",

author = "Fanny Grau and Bay{\'o}n, {J. Carles} and Aguirre, {Pedro A.} and Teodor Parella and Elisabet Du{\~n}ach",

year = "2008",

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doi = "10.1002/ejoc.200700881",

language = "English",

pages = "1214--1223",

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TY - JOUR

T1 - New aldehydes by catalytic diene cycloisomerisations

AU - Grau, Fanny

AU - Bayón, J. Carles

AU - Aguirre, Pedro A.

AU - Parella, Teodor

AU - Duñach, Elisabet

PY - 2008/3/1

Y1 - 2008/3/1

N2 - The Rh-catalysed hydroformylation of isopropylidenecyclohexane derivatives obtained by intramolecular diene cyclisations affords the corresponding aldehydes in good yields and in a completely chemo- and regioselective manner. Diastereoselectivities of ca. 90%were achieved for all substrates when a bulky phosphite was used as the Rh ligand. The stereochemical outcomes of the hydroformylation reactions were established by detailed NMR studies. The olfactory evaluation of the different aldehydes is also presented. © Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

AB - The Rh-catalysed hydroformylation of isopropylidenecyclohexane derivatives obtained by intramolecular diene cyclisations affords the corresponding aldehydes in good yields and in a completely chemo- and regioselective manner. Diastereoselectivities of ca. 90%were achieved for all substrates when a bulky phosphite was used as the Rh ligand. The stereochemical outcomes of the hydroformylation reactions were established by detailed NMR studies. The olfactory evaluation of the different aldehydes is also presented. © Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

KW - Aldehydes

KW - Hydroformylation

KW - Isopropylidenecyclohexane

KW - NMR spectroscopy

KW - Stereochemistry

U2 - 10.1002/ejoc.200700881

DO - 10.1002/ejoc.200700881

M3 - Article

SN - 1434-193X

SP - 1214

EP - 1223

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 7

ER -

New aldehydes by catalytic diene cycloisomerisations

Abstract

Keywords

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