ISSN:
0947-6539
Keywords:
asymmetric alkylations
;
chiral auxiliaries
;
kinetics
;
organolithium compounds
;
stereoselective syntheses
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Complexation of the configurationally labile α-phenylselenoalkyllithium compound 8 with 1,2-bisdimethylaminocyclohexane 15 led to two diastereomeric complexes 13 and 14 in a 7:3 ratio. Owing to ligand acceleration the complexes 13 and 14 added more rapidly to benzaldehyde than the uncomplexed organolithium compound 8. Trapping of complexes 13 and 14 by benzaldehyde was shown to occur more rapidly than their equilibration. This corresponds to non-Curtin-Hammett kinetics, in which enantiomeric enrichment in the products reflects the equilibrium ratio of the complexes 13 and 14.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.1460020612