Abstract Methyl groups in positions adjacent to an olefinic double bond can be metalated without cis/trans isomerisation. On the other hand configurational changes can be brought about via metalotropy; under equilibrium conditions the Z isomers (metal cis to an alkyl in β position) predominate overwhelmingly. This behaviour opens new stereoselective routes of high preparative utility.
[Laali, Khosrow; Gerzina, Robert J.; Flajnik, Christine M.; Geric, Cynthia M.; Dombroski, Ann Marie Helvetica Chimica Acta, 1987 , vol. 70, p. 607 - 611]