ENANTIOSELECTIVE SYNTHESIS OF SPIRO[4.5]DECANONE WITH 2-(S)-METHOXY-1,4-DIBROMOBUTANE

Authors
GALVEZ JMG ANGERS P CANONNE P
Citation
Jmg. Galvez et al., ENANTIOSELECTIVE SYNTHESIS OF SPIRO[4.5]DECANONE WITH 2-(S)-METHOXY-1,4-DIBROMOBUTANE, Tetrahedron letters, 35(18), 1994, pp. 2849-2852
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
18
Year of publication
1994
Pages
2849 - 2852
Database
ISI
SICI code
0040-4039(1994)35:18<2849:ESOSW2>2.0.ZU;2-W
Abstract
The reaction of 3-methyl-2-cyclohexen-1-one with 2-(S)-methoxy-1,4-dib romobutane (2) produced spiro[4.5]decanone 3, a key intermediate for t he synthesis of spirovetivanes, with regiodifferentiation and stereose lection. Subsequent addition of diisopropoxydimethyltitanium to the ca rbonyl group furnished compound 6 with diasterofacial selectivity. The same selectivity was observed in the subsequent catalytic hydrogenati on.