1032192-20-3Relevant academic research and scientific papers
Rhodium-catalyzed asymmetric formal cycloadditions of racemic butadiene monoxide with imines
Liu, Zhaoqun,Feng, Xiangqing,Du, Haifeng
supporting information; experimental part, p. 3154 - 3157 (2012/08/07)
A simple chiral sulfur-alkene hybrid ligand has proven to be highly effective for rhodium-catalyzed formal cycloaddition reactions of racemic butadiene monoxide and imines to furnish spirooxindole oxazolidines or 1,3-oxazolidines with high yields and stereoselectivities. A possible dynamic kinetic resolution as well as a kinetic resolution is considered to be involved in this catalytic process.
Oxazolidine synthesis by complementary stereospecific and stereoconvergent methods
Shaghafi, Michael B.,Grote, Robin E.,Jarvo, Elizabeth R.
, p. 5188 - 5191 (2011/12/15)
Complementary stereospecific and stereoconvergent reactions for enantioselective synthesis of 1,3-oxazolidines are reported. In the presence of a rhodium catalyst, reaction of enantioenriched butadiene monoxide with aryl imines is stereospecific (99% ee). Alternatively, the reaction of racemic butadiene monoxide, in the presence of a chiral palladium or nickel catalyst, provides an enantioselective synthesis of 1,3-oxazolidines (up to 94% ee). Synthesis of either the cis- or trans-1,3-oxazolidines is also accomplished under catalyst control.
Synthesis of nearly enantiopure allylic amines by aza-Claisen rearrangement of Z-configured allylic trifluoroacetimidates catalyzed by highly active ferrocenylbispalladacycles
Jautze, Sascha,Seiler, Paul,Peters, Rene
experimental part, p. 1430 - 1444 (2009/04/06)
The development of the first highly active enantioselective catalyst for the aza-Claisen rearrangement of Z-configured allylic trifluoroacetimidates generating valuable almost enantiopure protected allylic amines is described. Usually Z-configured allylic
Enantioselective iridium-catalyzed allylic aminations of allylic carbonates with functionalized side chains. Asymmetric total synthesis of (S)-vigabatrin
Gnamm, Christian,Franck, Geraldine,Miller, Nicole,Stork, Timon,Broedner, Kerstin,Helmchen, Guenter
experimental part, p. 3331 - 3350 (2009/05/27)
Indium-catalyzed aminations of allylic carbonates containing a variety of O-functional groups have been explored. High degrees of regio- as well as enantioselectivity were achieved with diacylamides under salt-free conditions and with arylamines. The results allowed the antiepilepsy drug (5)-vigabatrin to be prepared via a very short route.
