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A Comparative Study on the Diastereofacial Control in the [4+2] Cycloaddition of Sorbates and the Ene Reaction of Tiglates with Singlet Oxygen and PTAD by a Variety of Chiral Auxiliaries
Author(s) -
Adam Waldemar,
Bosio Sara G.,
Degen HansGeorg,
Krebs Oliver,
Stalke Dietmar,
Schumacher Dirk
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200212)2002:23<3944::aid-ejoc3944>3.0.co;2-4
Subject(s) - chemistry , singlet oxygen , ene reaction , cycloaddition , electrophile , menthol , organic chemistry , catalysis , oxygen
The auxiliary‐induced diastereoselectivities of [4+2] cycloaddition and the ene reaction of singlet oxygen and PTAD through a variety of auxiliaries is studied. The different trends in the diastereoselectivities that are observed for the diverse auxiliaries, which include 2,2‐dimethyloxazolidines, a menthol derivative, several related cyclohexanes, and the Oppolzer sultam, are compared and backed by mechanistic interpretations. From this overview of two reaction modes for two electrophiles and four different types of auxiliaries, the advantages of the individual auxiliaries become evident and comprehensible. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)