Tetrahedron Letters p. 849 - 852 (1986)
Update date:2022-08-22
Topics:
Chilot, Jean Jacques
Doutheau, Alain
Gore, Jacques
Saroli, Alfred
The cyclisation of allenic diols 3 and 4 in the presence of mercuric chloride or silver nitrate leads exclusively or predominantly to bicyclic acetals 6 and 8 resulting from an initial nucleophilic attack on the central allenic carbon.This regioselectivity depends on the presence of a terminal methylene in the unsaturation since diol 5 leads to the dihydropyrane 12 coming from the nucleophilic attack on the terminal allenic carbon.
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