Peer-Reviewed Journal Details
Mandatory Fields
Foley, VM;Cano, R;McGlacken, GP
2016
December
Tetrahedron: Asymmetry
The search for an easily-prepared sparteine surrogate
Validated
WOS: 2 ()
Optional Fields
C-2-SYMMETRIC TERTIARY DIAMINE CYCLIC CARBAMATE HYDRAZONES ASYMMETRIC-SYNTHESIS ENANTIOSELECTIVE DEPROTONATION AROMATIC IMINES (+)-SPARTEINE SURROGATES BOC-PYRROLIDINE O-ETHYLANILINE (-)-SPARTEINE KETONES
27
1160
1167
(-)-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 alpha-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. (C) 2016 Elsevier Ltd. All rights reserved.
OXFORD
0957-4166
10.1016/j.tetasy.2016.09.001
Grant Details