Diastereoselective synthesis of eight-membered-ring allenes from propargylic epoxides and aldehydes by silylene insertion into carbon-oxygen bonds

Christina Z. Rotsides, Chunhua Hu, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

Bent out of shape: Silver-catalyzed insertions of silylenes into propargylic C - O bonds of epoxides regioselectively form 1,2-silaoxetanes, which add to aldehydes to give the title allenes as single diastereomers (see scheme; Ts=4-toluenesulfonyl). An X-ray crystal structure confirmed the stereochemistry of the allene, which is bent significantly from linearity (164°).

Original languageEnglish (US)
Pages (from-to)13033-13036
Number of pages4
JournalAngewandte Chemie - International Edition
Volume52
Issue number49
DOIs
StatePublished - Dec 2 2013

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Stereochemistry
Epoxy Compounds
Aldehydes
Silver
Carbon
Crystal structure
Oxygen
X rays
propadiene

Keywords

  • allenes
  • medium-ring compounds
  • reactive intermediates
  • silicon
  • strained molecules

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Diastereoselective synthesis of eight-membered-ring allenes from propargylic epoxides and aldehydes by silylene insertion into carbon-oxygen bonds. / Rotsides, Christina Z.; Hu, Chunhua; Woerpel, Keith.

In: Angewandte Chemie - International Edition, Vol. 52, No. 49, 02.12.2013, p. 13033-13036.

Research output: Contribution to journalArticle

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