111806-71-4Relevant academic research and scientific papers
DIASTEREOSELECTIVE SYNTHESIS OF β- AND γ2-MUUROLENE: A CARBOCATIONIC PATHWAY FROM MONO- TO SESQUITERPENES
Azizur-Rahman,Klein, Herbert,Dressel, Juergen,Mayr, Herbert
, p. 6041 - 6046 (2007/10/02)
The Lewis acid catalysed addition of the piperityl chlorides 6 to isoprene yields adduct 7, which undergoes a cis-stereoselective cyclisation to give the diastereoisomeric muurolene monohydrochlorides 8.Treatment with potassium tert-butoxide affords β- an
Carvone- and Piperitone-Derived Allylic Stannanes and Aspects of Their Electrophilic Substitution
Young, David,Jones, Martin,Kitching, William
, p. 563 - 573 (2007/10/02)
cis- and trans-Carvotanacetols and -piperitols have been converted into the corresponding allylic chlorides, which were made to react with both trimethyltinlithium and triphenyltinlithium.The resulting allylic stannanes were characterized by 1H, 13C and 119Sn n.m.r. spectroscopy, which permitted assignment of the relative configurations.Triphenyltinlithium appears to react in a (substantially) concerted fashion with the (optically active) chloride from the carvotanacetols yielding an optically active stannane.The corresponding trimethylstannane is optically inactive.Substitution reactions (SE') with acid and sulfur dioxide (in chloroform) are preferentially γ-anti and specifically γ-syn respectively, in line with conclusions based on other cyclohex-2-enyl systems.
