In the process of investigating chiral auxiliaries for preparing enantiomerically pure SNF analogues via asymmetric 8p (8p, 6p) electrocyclization, we found that chiral oxazoline auxiliaries bearing trans aryl substituents could improve stereoselectivity in 8p electrocyclization up to 85 % (ee). And, the auxiliaries were readily removed by hydrolysis which can be converted into useful functional groups. Now we have applied our strategy to more generally acceptable system in 8p and 6p electrocyclization. This approach could allow not only to prepare enantiomerically pure bicyclo[4.2.0]octadiene and cyclohexadiene derivativies but also to understand nature of asymmetric electrocyclization.

Asymmetric electrocyclization induced by chiral oxazoline auxiliaries

240th National Meeting (2010)

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