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PtCl 4 ‐Catalyzed Domino Synthesis of Fused Bicyclic Acetals
Author(s) -
DiéguezVázquez Alejandro,
Tzschucke C. Christoph,
Lam Wing Yee,
Ley Steven V.
Publication year - 2007
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.200704595
Subject(s) - bicyclic molecule , domino , intramolecular force , alkyne , chemistry , aryl , toluene , catalysis , stereochemistry , medicinal chemistry , organic chemistry , alkyl
At sixes and sevens : The synthesis of [4.2.1]‐ and [3.2.1]‐fused bicyclic acetals by an intramolecular double alkoxylation of alkyne diols is reported. The course of the reaction depends on the substitution of the triple bond. Terminal alkynes give the [3.2.1]bicyclic product by a 6‐ exo pathway, whereas aryl alkynes undergo almost exclusively a 7‐ endo cyclization to give the [4.2.1]bicycles (see scheme, Ts=toluene‐4‐sulfonyl).