Affiliation:
1. Instituto de Química da Universidade de São Paulo, Av. Prof. Lineu Prestes 748, Cidade Universitária, São Paulo SP 05508 900, Brazil.
Abstract
Sulfinyltoluquinones (2a–2c) were submitted to thermal or catalyzed [4+2] cycloaddition reactions with cyclopentadiene. For p-tolylsulfinyltoluquinones (2b) and (2c), almost complete C2–C3-chemo- and unlike-diastereoselectivity was achieved by catalysis with ZnBr2, yielding adducts 6. Under thermal conditions, Diels–Alder reaction took place at the C5–C6 double bonds of quinones 2a–2c, generating mixtures of diastereoisomeric like- and unlike-adducts 4.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Reference56 articles.
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