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Gold Catalysis: β‐Ketonaphthalenes via Molecular Gymnastics of 1,6‐Diyne‐4‐en‐3‐ols
Author(s) -
Lauterbach Tobias,
Arndt Sebastian,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
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.201300396
Subject(s) - chemistry , alkyne , regioselectivity , ketone , catalysis , catalytic cycle , group (periodic table) , dual role , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry
1,6‐Diyne‐4‐en‐3‐ols with one terminal alkyne were applied as test substrates for a possible dual catalyzed cyclization. Instead of a dual catalysis cycle, naphthyl ketone derivatives were obtained as single products. The regioselectivity of the obtained products is unprecedented. Instead of the expected naphthyl ketones bearing the keto group in the α‐position, the keto group is positioned in the ß‐position of the naphthyl skeleton by a complex rearrangement of the starting materials.