LrgpV1, PubMed, Curation, bibRecord, 000148

Intramolecular cyclopropanation of unsaturated terminal epoxides and chlorohydrins.

Identifieur interne : 000148 ( PubMed/Curation ); précédent : 000147; suivant : 000149

Intramolecular cyclopropanation of unsaturated terminal epoxides and chlorohydrins.

Auteurs : David M. Hodgson [Royaume-Uni] ; Ying Kit Chung ; Irene Nuzzo ; Gloria Freixas ; Krystyna K. Kulikiewicz ; Ed Cleator ; Jean-Marc Paris

Source :

Journal of the American Chemical Society [ 0002-7863 ] ; 2007.

RBID : pubmed:17373790

Descripteurs français

KwdFr :
- Aldéhydes (), Catalyse, Chlorohydrines (), Composés époxy (), Cyclopropanes (), Heptanes (), Hexanes (), Isomérie, Sesquiterpènes (), Sesquiterpènes (synthèse chimique), Structure moléculaire.
MESH :
- synthèse chimique : Sesquiterpènes.
- Aldéhydes, Catalyse, Chlorohydrines, Composés époxy, Cyclopropanes, Heptanes, Hexanes, Isomérie, Sesquiterpènes, Structure moléculaire.

English descriptors

KwdEn :
- Aldehydes (chemistry), Bicyclo Compounds (chemistry), Catalysis, Chlorohydrins (chemistry), Cyclopropanes (chemistry), Epoxy Compounds (chemistry), Heptanes (chemistry), Hexanes (chemistry), Isomerism, Molecular Structure, Sesquiterpenes (chemical synthesis), Sesquiterpenes (chemistry).
MESH :
- chemical , chemical synthesis : Sesquiterpenes.
- chemical , chemistry : Aldehydes, Bicyclo Compounds, Chlorohydrins, Cyclopropanes, Epoxy Compounds, Heptanes, Hexanes, Sesquiterpenes.
- Catalysis, Isomerism, Molecular Structure.

Abstract

Lithium 2,2,6,6-tetramethylpiperidide (LTMP)-induced intramolecular cyclopropanation of unsaturated terminal epoxides provides an efficient and completely stereoselective entry to bicyclo[3.1.0]hexan-2-ols and bicyclo[4.1.0]heptan-2-ols. Further elaboration of C-5 and C-6 stannyl-substituted bicyclo[3.1.0]hexan-2-ols via Sn-Li exchange/electrophile trapping or Stille coupling generates a range of substituted bicyclic cyclopropanes. An alternative straightforward cyclopropanation protocol using a catalytic amount of 2,2,6,6-tetramethylpiperidine (TMP) allows for a convenient (1 g-7.5 kg) synthesis of bicyclo[3.1.0]hexan-2-ol and other bicyclic adducts. The synthetic utility of this chemistry has been demonstrated in a concise asymmetric synthesis of (+)-beta-cuparenone. The related unsaturated chlorohydrins also undergo intramolecular cyclopropanation via in situ epoxide formation.

DOI: 10.1021/ja0672932
PubMed: 17373790

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Le document en format XML

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<author><name sortKey="Hodgson, David M" sort="Hodgson, David M" uniqKey="Hodgson D" first="David M" last="Hodgson">David M. Hodgson</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. david.hodgson@chem.ox.ac.uk</nlm:affiliation>
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<wicri:regionArea>Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA</wicri:regionArea>
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<term>Bicyclo Compounds (chemistry)</term>
<term>Catalysis</term>
<term>Chlorohydrins (chemistry)</term>
<term>Cyclopropanes (chemistry)</term>
<term>Epoxy Compounds (chemistry)</term>
<term>Heptanes (chemistry)</term>
<term>Hexanes (chemistry)</term>
<term>Isomerism</term>
<term>Molecular Structure</term>
<term>Sesquiterpenes (chemical synthesis)</term>
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<term>Catalyse</term>
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<term>Cyclopropanes ()</term>
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<term>Structure moléculaire</term>
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<term>Sesquiterpenes</term>
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<term>Molecular Structure</term>
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<term>Chlorohydrines</term>
<term>Composés époxy</term>
<term>Cyclopropanes</term>
<term>Heptanes</term>
<term>Hexanes</term>
<term>Isomérie</term>
<term>Sesquiterpènes</term>
<term>Structure moléculaire</term>
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<front><div type="abstract" xml:lang="en">Lithium 2,2,6,6-tetramethylpiperidide (LTMP)-induced intramolecular cyclopropanation of unsaturated terminal epoxides provides an efficient and completely stereoselective entry to bicyclo[3.1.0]hexan-2-ols and bicyclo[4.1.0]heptan-2-ols. Further elaboration of C-5 and C-6 stannyl-substituted bicyclo[3.1.0]hexan-2-ols via Sn-Li exchange/electrophile trapping or Stille coupling generates a range of substituted bicyclic cyclopropanes. An alternative straightforward cyclopropanation protocol using a catalytic amount of 2,2,6,6-tetramethylpiperidine (TMP) allows for a convenient (1 g-7.5 kg) synthesis of bicyclo[3.1.0]hexan-2-ol and other bicyclic adducts. The synthetic utility of this chemistry has been demonstrated in a concise asymmetric synthesis of (+)-beta-cuparenone. The related unsaturated chlorohydrins also undergo intramolecular cyclopropanation via in situ epoxide formation.</div>
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Intramolecular cyclopropanation of unsaturated terminal epoxides and chlorohydrins.

Intramolecular cyclopropanation of unsaturated terminal epoxides and chlorohydrins.

Source :

Descripteurs français

English descriptors

Abstract

Links toward previous steps (curation, corpus...)

Links to Exploration step

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

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Pour générer des pages wiki