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The reactions of syn-1-haloethyl p-chlorophenyl sulfoxides (halogen=Cl, Br) with main-group organometallic reagents (n-BuMgCl, MeLi, n-BuLi, s-BuLi, and t-BuLi) in THF and PhMe solvents were examined. Product distributions were analyzed to determine the extent of competing sulfoxide ligand exchange, halogen–metal exchange, and deprotonation reaction pathways. A combination of t-BuLi in PhMe was optimal...
A novel method for the stereoselective preparation of 1-azaspiranes is described. Treatment of α- and β-substituted 3-(methoxyphenyl)-N-methoxypropionamides 1 with phenyliodine(III) bis(trifluoroacetate) initiates efficient azaspirocyclization, via a putative N-acylnitrenium ion intermediate, to provide cyclohexa-2,5 and 2,4-dienone spirolactams 8 and 11 with good π-facial selectivity. Furthermore,...
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