About: One-Pot Preparation of Chiral Carbacycles from Morita-Baylis-Hillman Carbonates by an Asymmetric Allylic Alkylation/Olefin Metathesis Sequence     Goto   Sponge   NotDistinct   Permalink

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Description
  • An operationally simple, one-pot synthetic protocol for the formation of all-carbon, highly substituted five- and six-membered rings is described. In this two-step procedure, an asymmetric allylic alkylation (AAA) of Morita-Baylis-Hillman (MBH) carbonates with allylmalononitrile, catalyzed by a chiral tertiary amine, is followed by a ring-closing alkene metathesis (RCM) reaction. Products are obtained in high yields, and an excellent level of optical purity of some of the target compounds is achieved after just a single recrystallization.
  • An operationally simple, one-pot synthetic protocol for the formation of all-carbon, highly substituted five- and six-membered rings is described. In this two-step procedure, an asymmetric allylic alkylation (AAA) of Morita-Baylis-Hillman (MBH) carbonates with allylmalononitrile, catalyzed by a chiral tertiary amine, is followed by a ring-closing alkene metathesis (RCM) reaction. Products are obtained in high yields, and an excellent level of optical purity of some of the target compounds is achieved after just a single recrystallization. (en)
Title
  • One-Pot Preparation of Chiral Carbacycles from Morita-Baylis-Hillman Carbonates by an Asymmetric Allylic Alkylation/Olefin Metathesis Sequence
  • One-Pot Preparation of Chiral Carbacycles from Morita-Baylis-Hillman Carbonates by an Asymmetric Allylic Alkylation/Olefin Metathesis Sequence (en)
skos:prefLabel
  • One-Pot Preparation of Chiral Carbacycles from Morita-Baylis-Hillman Carbonates by an Asymmetric Allylic Alkylation/Olefin Metathesis Sequence
  • One-Pot Preparation of Chiral Carbacycles from Morita-Baylis-Hillman Carbonates by an Asymmetric Allylic Alkylation/Olefin Metathesis Sequence (en)
skos:notation
  • RIV/00216208:11310/14:10282798!RIV15-MSM-11310___
http://linked.open...avai/riv/aktivita
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  • I
http://linked.open...iv/cisloPeriodika
  • 30
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  • 34573
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  • RIV/00216208:11310/14:10282798
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  • metathesis; Morita-Baylis-Hillman carbonates; asymmetric synthesis; organocatalysis (en)
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  • DE - Spolková republika Německo
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  • [FE8D51DF7F42]
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  • European Journal of Organic Chemistry
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  • neuveden
http://linked.open...iv/tvurceVysledku
  • Císařová, Ivana
  • Veselý, Jan
  • Tichá, Iveta
  • Putaj, Piotr Marek
http://linked.open...ain/vavai/riv/wos
  • 000343872900002
issn
  • 1434-193X
number of pages
http://bibframe.org/vocab/doi
  • 10.1002/ejoc.201402899
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  • 11310
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