Catalytic Asymmetric Nitroso‐Diels–Alder Reaction with Acyclic Dienes
2005; Wiley; Volume: 44; Issue: 43 Linguagem: Inglês
10.1002/anie.200501345
ISSN1521-3773
AutoresYuhei Yamamoto, Hisashi Yamamoto,
Tópico(s)Chemical Reaction Mechanisms
ResumoBigger, bulkier, better: Catalytic asymmetric nitroso-Diels–Alder reactions of nitrosopyridines with silyloxydienes lead to adducts with excellent enantioselectivities (see scheme). The bulk of the silyl group (TMS=trimethylsilyl, TIPS=triisopropylsilyl) forces the diene to adopt an s-cis configuration in favor of the typical concerted [4+2] cycloaddition. The Diels–Alder adducts can then be converted into protected amino alcohols. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z501345_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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