Insertions of silylenes into vinyl epoxides: Diastereoselective synthesis of functionalized, optically active trans-dioxasilacyclooctenes

Michel Prévost, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) This communication describes a direct route to functionalized nonracemic trans-dioxasilacyclooctenes that involves stereoselective silylene insertions into vinyl epoxides to provide vinyl silaoxetane intermediates. These strained allylic silanes then undergo uncatalyzed allylation of aldehydes to afford trans-dioxasilacyclooctenes. Diastereoselective additions to these alkenes allow efficient transfer of planar chirality to chirality at stereogenic carbon atoms.

Original languageEnglish (US)
Pages (from-to)14182-14183
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number40
DOIs
StatePublished - Oct 14 2009

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Silanes
Chirality
Epoxy Compounds
Alkenes
Aldehydes
Carbon
Allylation
Olefins
Atoms
Communication

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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abstract = "(Chemical Equation Presented) This communication describes a direct route to functionalized nonracemic trans-dioxasilacyclooctenes that involves stereoselective silylene insertions into vinyl epoxides to provide vinyl silaoxetane intermediates. These strained allylic silanes then undergo uncatalyzed allylation of aldehydes to afford trans-dioxasilacyclooctenes. Diastereoselective additions to these alkenes allow efficient transfer of planar chirality to chirality at stereogenic carbon atoms.",
author = "Michel Pr{\'e}vost and Keith Woerpel",
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doi = "10.1021/ja906204a",
language = "English (US)",
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AU - Woerpel, Keith

PY - 2009/10/14

Y1 - 2009/10/14

N2 - (Chemical Equation Presented) This communication describes a direct route to functionalized nonracemic trans-dioxasilacyclooctenes that involves stereoselective silylene insertions into vinyl epoxides to provide vinyl silaoxetane intermediates. These strained allylic silanes then undergo uncatalyzed allylation of aldehydes to afford trans-dioxasilacyclooctenes. Diastereoselective additions to these alkenes allow efficient transfer of planar chirality to chirality at stereogenic carbon atoms.

AB - (Chemical Equation Presented) This communication describes a direct route to functionalized nonracemic trans-dioxasilacyclooctenes that involves stereoselective silylene insertions into vinyl epoxides to provide vinyl silaoxetane intermediates. These strained allylic silanes then undergo uncatalyzed allylation of aldehydes to afford trans-dioxasilacyclooctenes. Diastereoselective additions to these alkenes allow efficient transfer of planar chirality to chirality at stereogenic carbon atoms.

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