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Constructing Tricyclic Compounds Containing a Seven‐Membered Ring by Ruthenium‐Catalyzed Intramolecular [5+2] Cycloaddition
Author(s) -
Trost Barry M.,
Shen Hong C.
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20010618)40:12<2313::aid-anie2313>3.0.co;2-h
Subject(s) - intramolecular force , cycloaddition , ruthenium , regioselectivity , tricyclic , ring (chemistry) , chemistry , catalysis , enyne , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry
Efficient access to tricyclic compounds such as 2 and 3 , which contain a seven‐membered ring, is provided by the ruthenium‐catalyzed intramolecular [5+2] cycloaddition of a 1,2,3‐trisubstituted cyclopropyl enyne such as 1 . Improved regioselectivity is observed when In(OTf) 3 is used as the cocatalyst. (No cocatalyst: 2 : 3 6:1; cat. In(OTf) 3 (10 %): 2 : 3 >20:1; Tf=trifluoromethanesulfonyl).