Synthesis 2000; 2000(6): 899-903
DOI: 10.1055/s-2000-6268
special topic
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

An Efficient Strategy for the Synthesis of α,α′-cis and trans-Disubstituted Medium Ring Ethers

Michael T. Crimmins* , Kyle A. Emmitte
  • *Venable and Kenan Laboratories of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA; Fax +1 (9 19) 9 62 23 88; E-mail:
Further Information

Publication History

Publication Date:
31 December 2000 (online)

An asymmetric alkylation-ring-closing metathesis strategy was developed for the construction of α,α′-disubstituted medium ring ethers. The approach features an asymmetric alkylation of highly functionalized α-alkoxy acyl oxazolidinones followed by ring closure effected by Grubbs' ruthenium catalyst. The relationship between diene conformation and the rate of ring-closure was examined.