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Chiral 4-(Diphenylphosphanyl)-1-(dialkylamino)butane Ligands - Synthesis, Applications in Asymmetric Alkylation and Theoretical Study (2000)

Robert, Fabien ; Delbecq, Françoise ; Nguefack, Christelle ; [et al.]

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 2000 (2000), S. 351-358

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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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