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Gold(I)‐Catalyzed Access to Tetrahydropyran‐4‐ones from 4‐(Alkoxyalkyl)oxy‐1‐butynes: Formal Catalytic Petasis–Ferrier Rearrangement
Author(s) -
Bae Hyo Jin,
Jeong Wook,
Lee Ji Hyung,
Rhee Young Ho
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201002918
Subject(s) - phosphine , tetrahydropyran , catalysis , ligand (biochemistry) , chemistry , catalytic cycle , combinatorial chemistry , computer science , organic chemistry , ring (chemistry) , biochemistry , receptor
Gold cycle redesigned : By utilizing the alkynophilic effect of gold(I) complexes, a new method for the synthesis of highly substituted cis ‐2,6‐tetrahydropyranones was developed, which represents a catalytic surrogate of the Petasis–Ferrier rearrangement (see scheme). Of particular interest is the unique effect the phosphine ligand has on the diastereoselectivity of the alkyl groups at the 2‐ and 6‐positions.