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Gold(III) Chloride‐Catalyzed 6‐ endo ‐ trig Oxa‐Michael Addition Reactions for Diastereoselective Synthesis of Fused Tetrahydropyranones
Author(s) -
Ciesielski Jennifer,
Lebœuf David,
Stern Harry A.,
Frontier Alison J.
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300265
Subject(s) - chemistry , boron trifluoride , catalysis , intramolecular force , ring (chemistry) , aldol reaction , medicinal chemistry , michael reaction , chloride , boron , addition reaction , organic chemistry
Alkynones were treated with boron trifluoride diethyl etherate to generate β‐iodoallenolates, which underwent intramolecular aldol reactions to produce cycloalkenyl alcohols. Diastereoselective oxa‐Michael ring closure could then be induced by treatment with a catalytic amount of gold(III) chloride, affording highly functionalized tetrahydropyranone‐containing ring systems.