PALLADIUM-CATALYZED CROSS-COUPLING OF VINYL TRIFLATES WITH 9-ALKYL-9-BOROBICYCLO[3,3,1]NONANES - TOTAL SYNTHESIS OF (-)-ISOSEIRIDINE

Authors
GRIGG R KENNEWELL P SAVIC V
Citation
R. Grigg et al., PALLADIUM-CATALYZED CROSS-COUPLING OF VINYL TRIFLATES WITH 9-ALKYL-9-BOROBICYCLO[3,3,1]NONANES - TOTAL SYNTHESIS OF (-)-ISOSEIRIDINE, Tetrahedron, 50(18), 1994, pp. 5489-5494
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
18
Year of publication
1994
Pages
5489 - 5494
Database
ISI
SICI code
0040-4020(1994)50:18<5489:PCOVTW>2.0.ZU;2-4
Abstract
Pd(O) Catalysed cross-coupling of butenolide-3-triflates to 9-alkyl-9- borobicyclo[3.3.1] nonanes occurs in moderate to good yield and tolera tes a range of functionality. Application of this methodology combined with addition of diethylzinc to a butenolide aldehyde in the presence of on ephedrine derivative leads to a 3-step synthesis of (-)-isoseir idine with 88%e.e. in good yield.