Fluoride ion mediated cyclization of aldehydes (1 and 2) having regioisomeric allylsilane functionalities give a mixture of cis- and trans-isopiperitenol (3). The aldehydes (1) reacted faster and showed better stereoselectivity than the regioisomeric aldehydes (2) regardless of geometry of the double bond at an unsaturated aldehyde.
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Nakamura et al. (1992) studied this question.
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