X=Y=ZH Systems as potential 1,3-dipoles. Part 58: Cycloaddition route to chiral conformationally constrained (R)-pro-(S)-pro peptidomimetics |
| |
| Authors: | HAli Dondas Ronald Grigg Colin Kilner |
| |
| Institution: | a Department of Chemistry, Molecular Innovation, Diversity and Automated Synthesis (MIDAS) Centre, School of Chemistry, The University of Leeds, Leeds LS2 9JT, UK
b Department of Chemistry, Faculty of Pharmacy, Mersin University, 33342 Mersin, Turkey |
| |
| Abstract: | Imines of (1S,9S)-t-butyl-9-amino-octahydro-6,10-dioxo-6H-pyridazino1,2-a]1,2]diazepine-1-carboxylate undergo thermal (toluene, 110°C) or LiBr-DBU catalysed (MeCN, room temperature) regio- and stereo-specific cycloaddition to a range of chiral dipolarophiles giving enantiopure spiro-cycloadducts in excellent yield. The reactions proceed via intermediate NH azomethine ylides and litho azomethine ylides, respectively and results in the multiplication of chiral centres from 2 (one of which is lost in the process) to 5. |
| |
| Keywords: | cilazapril ACE inhibitors imines azomethine ylide 1 3-dipolar cycloaddition peptidomimetics multiplication of chirality |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
