A double ring closing metathesis reaction in the rapid, enantioselective synthesis of NK-1 receptor antagonists

Authors
Wallace, DJ Goodman, JM Kennedy, DJ Davies, AJ Cowden, CJ Ashwood, MS Cottrell, IF Dolling, UH Reider, PJ
Citation
Dj. Wallace et al., A double ring closing metathesis reaction in the rapid, enantioselective synthesis of NK-1 receptor antagonists, ORG LETT, 3(5), 2001, pp. 671-674
Citations number
26
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
5
Year of publication
2001
Pages
671 - 674
Database
ISI
SICI code
1523-7060(20010308)3:5<671:ADRCMR>2.0.ZU;2-R
Abstract
[GRAPHICS] The NK-1 receptor antagonist 1 has been prepared in seven steps from phenyl glycine methyl ester. The key steps are a double ring closing metathesis re action of tetraene 7 to prepare spirocycle 6 and a reductive Heck reaction to introduce the aryl moiety. This latter reaction discriminates the olefin s of compound 6 and proceeds in a highly regio- and stereoselective manner.