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Stereoselective Cyclization of 4‐Substituted 5‐Hexen‐1‐ols and Related Compounds by Benzeneselenenyl Triflate
Author(s) -
Inoue Hirohumi,
Murata Shizuaki,
Suzuki Toshiyasu
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940910
Subject(s) - chemistry , stereoselectivity , trifluoromethanesulfonate , steric effects , alkoxy group , intramolecular force , stereochemistry , alkyl , cis–trans isomerism , medicinal chemistry , organic chemistry , catalysis
Oxyselenylation of 4‐substituted 5‐hexen‐1‐ols 1 with benzeneselenenyl trifluoromethanesulfonate proceeds by intramolecular exo cyclization stereoselectively to give 3‐substituted trans ‐ or cis ‐2‐(phenylselenenylmethyl)tetrahydropyrans 3 . Formation of the trans isomers is favored when the substituents contain alkyl or phenyl substituents in the 4‐position, whereas the cis isomers predominate when the substituents are alkoxyalkyl, alkoxyl, acyl, and hydroxyl. The mechanism of the trans and cis stereoselectivity is explained by steric and electronic effects in the phenylseleniranium intermediates, 7 and 8 .