A new class of chiral P,N-ligands and their application in palladium-catalyzed asymmetric allylic substitution reactions

Journal of Organic Chemistry

Volumn 69, Issue 15, 2004, Pages 5060-5064

  Lyle, Michael P A ^a   Narine, Arun A ^a   Wilson, Peter D ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CATALYTIC ASYMMETRIC SYNTHESIS; MODULAR SYNTHESIS;

ORGANIC COMPOUNDS;

2 CHLORO 4 METHYL 6,7 DIHYDRO 5H [1]PYRINDIN 7 ONE; ACETAL; ACETIC ACID; ALLYL COMPOUND; ETHYLENE GLYCOL; LIGAND; MALONIC ACID; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHEMICAL ANALYSIS; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 3543022706     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0494275     Document Type: Article

References (30)

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19. 4] was employed as a catalyst for this reaction in the first instance. The reactions were performed at reflux in benzene or toluene with potassium carbonate as the base.
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27. 1HNMR techniques. Of note, other isomers of π-allyl complexes are possible. However, M- and W-isomers are assumed to be the mechanistically relevant π-allyl intermediates; for discussion, see ref 3b.
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29. The strong trans-effect of the phosphine donor relative to the pyridine donor is well-established in related P,N-ligands; see ref 2.
30. This stereochemical assumption was based on inspection of molecular models of the M- and W-isomer of the π-allyl intermediate as discussed earlier; see also footnote 21.