137496-67-4Relevant articles and documents
Assymetric Deprotonations: Enantioselective Syntheses of 2-Substituted (tert-Butoxycarbonyl)pyrrolidines
Kerrick, Shawn T.,Beak, Peter
, p. 9708 - 9710 (1991)
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The search for an easily-prepared sparteine surrogate
Foley, Vera M.,Cano, Rafael,McGlacken, Gerard P.
, p. 1160 - 1167 (2016/11/04)
(?)-Sparteine has proven itself to be a highly efficient and versatile ligand. However, in recent years it has become difficult to source. In addition the (+)-enantiomer is also not readily available. Here we report a suite of chiral diamines as potential sparteine surrogates. Chiral trans-1,2-diaminocyclohexane is commercially available in both enantiomeric forms and the parent structure can be easily modified. New (and known) chiral diamines have been tested in the asymmetric silylation of N-Boc pyrrolidine, N-Boc piperidine, the α-alkylation of dimethylhydrazones and in the rearrangement of meso-epoxides. While none match the selectivity of the highly evolved natural product, there is certainly potential for this class of diamine ligands to perform in a diverse set of asymmetric transformations.
Evaluation of the chiral DIANANE backbone as ligand for organolithium reagents
Praz, Jezabel,Guenee, Laure,Aziz, Sarwar,Berkessel, Albrecht,Alexakis, Alexandre
supporting information; experimental part, p. 1780 - 1790 (2012/07/28)
Novel endo,endo-2,5-diaminonorbonane-derived tertiary C2- symmetrical diamines were synthesized via the one-pot reductive amination of enantiomerically pure norbornane-2,5-dione. These ligands were applied to various catalytic reactions such as asymmetric deprotonation, asymmetric bromine-lithium exchange, and enantioselective addition of aryl- and allkylithium reagents to aromatic aldimines. Copyright
