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ChemInform Abstract: Diastereoselective Zwitterionic Aza-Claisen Rearrangement: Synthesis of Nine-Membered Ring Lactams and Transannular Ring Contraction.

โœ Scribed by M. DIEDERICH; U. NUBBEMEYER


Book ID
112039540
Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
27
Category
Article
ISSN
0931-7597

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Unusual Diastereoselection in the Synthe
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The aza-Claisen rearrangement of vinylpyrrolidines 1 yielded almost exclusively the trans-3,8-disubstituted nine-membered ring lactams 2 (TBS=tBuMe Si), independent of whether cis or trans isomers were used as starting materials. The conformation (which provided facial chirality) of the medium-sized