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Chemoselectivity in the Pd‐Catalyzed Cyclization of 1,6‐Enynes and Proof of the Relative Configuration of the New Stereogenic Centers
Author(s) -
Trost Barry M.,
Hashmi A. Stephen K.,
Ball Richard G.
Publication year - 2001
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 - 10.1002/1615-4169(200107)343:5<490::aid-adsc490>3.0.co;2-s
Subject(s) - stereocenter , chemistry , enyne , chemoselectivity , catalysis , stereochemistry , bicyclic molecule , substructure , combinatorial chemistry , organic chemistry , enantioselective synthesis , structural engineering , engineering
The dimerization of dienyne 6 with a palladole catalyst readily provides the bicyclic enyne rac ‐ 7 . A second cyclization of the 1,6‐enyne substructure in rac ‐ 7 works best with a hydropalladation catalyst and delivers rac ‐ 8 . Diels‐Alder reactions of the latter finally lead to a crystalline product rac ‐ 12 . A crystal structure analysis of rac ‐ 12 allowed the determination of the relative configuration of all stereogenic centers formed in the dimerization of 6 .