Abstract

Functionalized allylsilanes 1– 5 and aldehydes 6– 8 undergo Lewis-acid mediated ring closure to afford 2,3,5- or 6-substituted tetrahydropyrans ( 8– 15 ) and 2,3-substituted octahydrochromenes ( 16a– b ) with excellent stereoselectivity. According to DFT calculations the high stereoselectivity arises from electronically induced steric effects occurring in the key-intermediate of the cyclization.

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