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Unusual Diastereoselection in the Synthesis of Nine‐Membered Ring Lactams and Conformation‐Controlled Transannular Reactions to Generate Optically Active Indolizidinones
Author(s) -
Sudau Alexander,
Nubbemeyer Udo
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980504)37:8<1140::aid-anie1140>3.0.co;2-w
Subject(s) - ring (chemistry) , stereochemistry , optically active , chirality (physics) , chemistry , chiral symmetry , organic chemistry , physics , quantum mechanics , nambu–jona lasinio model , quark
The aza‐Claisen rearrangement of vinylpyrrolidines 1 yielded almost exclusively the trans ‐3,8‐disubstituted nine‐membered ring lactams 2 (TBS= t BuMe 2 Si), independent of whether cis or trans isomers were used as starting materials. The conformation (which provided facial chirality) of the medium‐sized ring controlled the regio‐ and diastereoselectivities of the transannular reactions that afforded indolizidinones 3 .