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Gold Catalysis: Efficient 1,3‐Induction with Diastereotopic Homopropargyl Alcohols in the Phenol Synthesis
Author(s) -
Hashmi A. Stephen K.,
Hamzić Melissa,
Rudolph Matthias,
Ackermann Martin,
Rominger Frank
Publication year - 2009
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.200900402
Subject(s) - chemistry , cyclohexene , alkyl , phenols , phenol , catalysis , asymmetric induction , ring (chemistry) , organic chemistry , medicinal chemistry , stereochemistry , enantioselective synthesis
Furans with diastereotopic alkynyl groups were prepared and then converted to anellated phenols in gold‐catalyzed reactions. In all cases a highly diastereoselective reaction was observed. The stereochemical outcome of the 1,3‐induction could be assigned by two independent crystal structure analyses, showing a cis ‐arrangement of the two alkyl substituents on the benzoanellated cyclohexene ring.