CHIRAL SYNTHONS FROM CARVONE .11. A REGIOSPECIFIC RADICAL ANNULATION STRATEGY TO FUNCTIONALIZED CHIRAL BICYCLO[3.3.1]NONANES

Authors
SRIKRISHNA A HEMAMALINI P VENKATESWARLU S
Citation
A. Srikrishna et al., CHIRAL SYNTHONS FROM CARVONE .11. A REGIOSPECIFIC RADICAL ANNULATION STRATEGY TO FUNCTIONALIZED CHIRAL BICYCLO[3.3.1]NONANES, Tetrahedron, 50(29), 1994, pp. 8781-8792
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
29
Year of publication
1994
Pages
8781 - 8792
Database
ISI
SICI code
0040-4020(1994)50:29<8781:CSFC.A>2.0.ZU;2-C
Abstract
A radical annulation, i.e. an intermolecular radical Michael addition followed by an intramolecular Michael addition of the resultant radica l (radical cyclisation) has been employed for the construction of chir al functionalised bicyclo[3.3,1]-nonanes. Thus reaction of carvone hyd rohalides 7 with (n)Bu(3)SnH and AIBN in the presence of excess of rad icophiles 4 furnished, regiospecifically bicyclo[3.3.1]nonanes 8-14, i ntroducing three new chiral centres in a stereoselective manner. Analo gously the bromide 18 generated the bridgehead substituted bicyclo[3.3 .1]-nonanes 19-21.