DEVELOPMENT OF A TITANOCENE-CATALYZED ENYNE CYCLIZATION ISOCYANIDE INSERTION REACTION

Authors
BERK SC GROSSMAN RB BUCHWALD SL
Citation
Sc. Berk et al., DEVELOPMENT OF A TITANOCENE-CATALYZED ENYNE CYCLIZATION ISOCYANIDE INSERTION REACTION, Journal of the American Chemical Society, 116(19), 1994, pp. 8593-8601
Citations number
62
Categorie Soggetti
Chemistry
Journal title
Journal of the American Chemical Society → ACNP
ISSN journal
00027863
Volume
116
Issue
19
Year of publication
1994
Pages
8593 - 8601
Database
ISI
SICI code
0002-7863(1994)116:19<8593:DOATEC>2.0.ZU;2-F
Abstract
The first early transition metal-catalyzed enyne cyclization reaction is described. The system converts enyne substrates to bicyclic iminocy clopentenes through the use of 10 mol % of Cp(2)Ti(PMe(3))(2) in the p resence of a silyl cyanide. Subsequent hydrolysis produces the corresp onding bicyclic cyclopentenones in good overall yield. The cyclization reaction is tolerant of polar functional groups such as ethers, amine s, and esters and is diastereoselective with certain chiral enyne subs trates.