ISSN:
1434-1948
Keywords:
Aminophosphanes
;
Palladium
;
Alkylations
;
Enantioselectivity
;
Theoretical study
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Various 4-(diphenylphosphanyl)-1-(dialkylamino)butane ligands were prepared from commercial (2S,3S)-2,3-O-isopropylidene-D-threitol. These ligands, associated with Pd2(dba)3, gave enantioselectivities of up to 75% in the alkylation of racemic 1,3-diphenylprop-2-enyl acetate with dimethyl malonate anion. A theoretical study shows the important role played by two factors in the alkylation reaction: steric control, leading to the formation of a unique diastereoisomer of the π-allylpalladium complex, and orbital control, which orients the attack of the nucleophile trans to the phosphorus atom.
Additional Material:
6 Ill.
Type of Medium:
Electronic Resource
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