(3R,4R,5S)-4-Hydr­oxy-3-methyl-5-[(2S,3R)-3-methyl­pent-4-en-2-yl]-4,5-dihydro­furan-2(3H)-one

The relative configuration of the title compound, C(11)H(18)O(3), which was synthesized using a catalytic asymmetric Gosteli–Claisen rearrangement, a diastereoselective reduction with K-Selectride and an Evans aldol addition, was corroborated by single-crystal X-ray diffraction analysis. The five-me...

Descripción completa

Detalles Bibliográficos
Autores principales: Gille, Annika, Schürmann, Markus, Preut, Hans, Hiersemann, Martin
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2971977/
https://www.ncbi.nlm.nih.gov/pubmed/21578968
http://dx.doi.org/10.1107/S1600536809050399
_version_ 1782190714749190144
author Gille, Annika
Schürmann, Markus
Preut, Hans
Hiersemann, Martin
author_facet Gille, Annika
Schürmann, Markus
Preut, Hans
Hiersemann, Martin
author_sort Gille, Annika
collection PubMed
description The relative configuration of the title compound, C(11)H(18)O(3), which was synthesized using a catalytic asymmetric Gosteli–Claisen rearrangement, a diastereoselective reduction with K-Selectride and an Evans aldol addition, was corroborated by single-crystal X-ray diffraction analysis. The five-membered ring has an envelope conformation with a dihedral angle of 29.46 (16)° between the coplanar part and the flap (the hydr­oxy-bearing ring C atom). In the crystal, mol­ecules are connected via bifurcated O—H⋯(O,O) hydrogen bonds, generating [010] chains.
format Text
id pubmed-2971977
institution National Center for Biotechnology Information
language English
publishDate 2009
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-29719772010-12-30 (3R,4R,5S)-4-Hydr­oxy-3-methyl-5-[(2S,3R)-3-methyl­pent-4-en-2-yl]-4,5-dihydro­furan-2(3H)-one Gille, Annika Schürmann, Markus Preut, Hans Hiersemann, Martin Acta Crystallogr Sect E Struct Rep Online Organic Papers The relative configuration of the title compound, C(11)H(18)O(3), which was synthesized using a catalytic asymmetric Gosteli–Claisen rearrangement, a diastereoselective reduction with K-Selectride and an Evans aldol addition, was corroborated by single-crystal X-ray diffraction analysis. The five-membered ring has an envelope conformation with a dihedral angle of 29.46 (16)° between the coplanar part and the flap (the hydr­oxy-bearing ring C atom). In the crystal, mol­ecules are connected via bifurcated O—H⋯(O,O) hydrogen bonds, generating [010] chains. International Union of Crystallography 2009-11-28 /pmc/articles/PMC2971977/ /pubmed/21578968 http://dx.doi.org/10.1107/S1600536809050399 Text en © Gille et al. 2009 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Gille, Annika
Schürmann, Markus
Preut, Hans
Hiersemann, Martin
(3R,4R,5S)-4-Hydr­oxy-3-methyl-5-[(2S,3R)-3-methyl­pent-4-en-2-yl]-4,5-dihydro­furan-2(3H)-one
title (3R,4R,5S)-4-Hydr­oxy-3-methyl-5-[(2S,3R)-3-methyl­pent-4-en-2-yl]-4,5-dihydro­furan-2(3H)-one
title_full (3R,4R,5S)-4-Hydr­oxy-3-methyl-5-[(2S,3R)-3-methyl­pent-4-en-2-yl]-4,5-dihydro­furan-2(3H)-one
title_fullStr (3R,4R,5S)-4-Hydr­oxy-3-methyl-5-[(2S,3R)-3-methyl­pent-4-en-2-yl]-4,5-dihydro­furan-2(3H)-one
title_full_unstemmed (3R,4R,5S)-4-Hydr­oxy-3-methyl-5-[(2S,3R)-3-methyl­pent-4-en-2-yl]-4,5-dihydro­furan-2(3H)-one
title_short (3R,4R,5S)-4-Hydr­oxy-3-methyl-5-[(2S,3R)-3-methyl­pent-4-en-2-yl]-4,5-dihydro­furan-2(3H)-one
title_sort (3r,4r,5s)-4-hydr­oxy-3-methyl-5-[(2s,3r)-3-methyl­pent-4-en-2-yl]-4,5-dihydro­furan-2(3h)-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2971977/
https://www.ncbi.nlm.nih.gov/pubmed/21578968
http://dx.doi.org/10.1107/S1600536809050399
work_keys_str_mv AT gilleannika 3r4r5s4hydroxy3methyl52s3r3methylpent4en2yl45dihydrofuran23hone
AT schurmannmarkus 3r4r5s4hydroxy3methyl52s3r3methylpent4en2yl45dihydrofuran23hone
AT preuthans 3r4r5s4hydroxy3methyl52s3r3methylpent4en2yl45dihydrofuran23hone
AT hiersemannmartin 3r4r5s4hydroxy3methyl52s3r3methylpent4en2yl45dihydrofuran23hone

Ejemplares similares