Premium
Palladium/Lewis Acid‐Catalyzed Reactions of Bicyclic Hydrazines with Organostannanes: A General Methodology for the Stereoselective Synthesis of 3,4‐Disubstituted Cyclopentenes
Author(s) -
Sajisha V. S.,
Radhakrishnan K. V.
Publication year - 2006
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.200505488
Subject(s) - chemistry , stereoselectivity , bicyclic molecule , lewis acids and bases , catalysis , palladium , vicinal , organic chemistry , ring (chemistry) , combinatorial chemistry
Pd/Lewis acid‐catalyzed reactions of bicyclic hydrazines with organostannanes afforded the 3,4‐disubstituted cyclopentenes in excellent yields. The reaction is milder and is the first general methodology developed for the stereoselective synthesis of trans , vicinal disubstituted cyclopentenes. The results show that organostannanes with easily functionalizable moieties can be efficiently utilized in the ring opening of bicyclic hydrazines leading to the stereoselective formation of 3,4‐disubstituted cyclopentenes. The products, having a wide range of substituents, are important intermediates in the synthesis of biologically active molecules like cyclopentenyl nucleosides, glycosidase inhibitors etc.