Cleavage of a chiral auxiliary using RCM on an especially sterically crowded alkene: Syntheses of chiral carbo- and heterocycles
Journal of Organometallic Chemistry
Chiral 1,5-, 1,6-, and 1,7-dienes generated in 3–4 steps from chiral auxiliary p-menthane-3-carboxaldehyde undergo RCM with notable discrepancies in reactivity depending on the nature and number of substituents flanking the central double bond. The chiral auxiliary is thus cleaved releasing a carbo- or heterocycle in the process. Special features concerning the RCM on these especially crowded systems are discussed.
Spino, C, L Boisvert, J Douville, S Roy, S Lauzon, J Minville, D Gagnon, F Beaumier, and C Chabot. "Cleavage of a Chiral Auxiliary Using Rcm on an Especially Sterically Crowded Alkene: Syntheses of Chiral Carbo and Heterocycles." Journal of Organometallic Chemistry. 691 (2006): 5336-5355. Print.