E. Vilsmaier, M. Dotzauer, R. Wagemann
Oct 9, 1995
Citations
0
Influential Citations
6
Citations
Journal
Tetrahedron
Abstract
Abstract Dimorpholinobicyclo[3.1.0]hexanecarbonitrile diastereomers 1a and 8a have been synthesized with high stereoselectivity starting from dichloroenamines 11 and 13 . The sequence 11 → 17 → 19 and reductive amination of the latter provided isomer 1a . Ring closure of 13 by cyanide and subsequent dechlorination of 14 produced compound 8a . The stereochemistry of the cyclopropane forming reaction was studied using cis and trans isomers of chloroenamine 12 : trans 12-t gave almost exclusively 3 α -morpholine derivatives 4a / 8a upon interaction of cyanide. Cis 12-c led to 3 α - and 3 β -morpholine products 4a / 8a and 1a / 5a in a ratio of 3:1 indicating an aminoallylcation intermediate 30 in the former case. Cis-configuration of chloroenamine isomer 12-c was established by X-ray structural analysis.