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Efficient Oxidative Cyclization of 1,6‐Dienes: A Highly Diastereoselective Entry to Substituted Tetrahydropyrans
Author(s) -
Roth Stefanie,
Stark Christian B. W.
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200504572
Subject(s) - sodium periodate , tetrahydropyran , chemistry , oxidative phosphorylation , catalysis , periodate , combinatorial chemistry , organic chemistry , ring (chemistry) , biochemistry
Widely applicable : Substituted tetrahydropyran products can be obtained in good to high yields and excellent diastereoselectivity by oxidative cyclization of 1,6‐dienes (see scheme, PG=protecting group). In situ generated ruthenium tetroxide (1–5 mol %) serves as a catalyst and sodium periodate on wet silica serves as a terminal oxidant. The conversion of a cyclization product into a synthetically useful δ‐lactone building block is also presented.
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