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Acyclic Stereocontrol via Organogembismetallic Reagents; Part III1
08 March 2002 (online)
The metalla-Claisen reaction leads under very mild conditions, high chemical yields and diastereoselectivity to compounds with two adjacent asymmetric centers. For example, (Z)-1-heptenyllithium (2) was converted into (3S,4R)-3,4-dimethyl-1-nonene (5) by reaction with crotylmagnesium bromide and zinc(II) bromide and subsequent hydrolysis of the gem-1,1-bismetallic intermediate 4.