On the Synthesis and Addition Reactions of Chiral N-Heterocyclic Diphosphines

Reaction of chiral N-heterocyclic chlorophosphines with lithium diphenylphosphide or of achiral N-heterocyclic chlorophosphines with optically active lithium menthyl phosphide produces chiral N-heterocyclic diphosphines which can be utilized in subsequent diphosphination reactions with activated alk...

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Vydáno v:Zeitschrift für Naturforschung. B, A journal of chemical sciences Ročník 67; číslo 8; s. 765 - 773
Hlavní autoři: Foerster, Daniela, Hartenbach, Ingo, Nieger, Martin, Gudat, Dietrich
Médium: Journal Article
Jazyk:angličtina
Vydáno: BERLIN Walter De Gruyter 01.08.2012
Témata:
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
1ST RESOLUTION
PHOSPHORUS
PHOSPHINE
COMPLEXES
Diphosphines
HIGHLY ENANTIOSELECTIVE HYDROFORMYLATION
Chiral Ligands
N-Heterocyclic Phosphines
BIS(TRIARYL)PHOSPHINE
LIGANDS
Diphosphination
ALPHA-(ACYLAMINO)ACRYLIC ACIDS
2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL BINAP
ASYMMETRIC HYDROGENATION
Phosphine Complexes
ISSN:0932-0776, 1865-7117
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Popis
Shrnutí:Reaction of chiral N-heterocyclic chlorophosphines with lithium diphenylphosphide or of achiral N-heterocyclic chlorophosphines with optically active lithium menthyl phosphide produces chiral N-heterocyclic diphosphines which can be utilized in subsequent diphosphination reactions with activated alkenes or alkynes. The reaction with alkynes proceeds stereospecifically to produce Z-ethylene-1,2-bisphosphines which are readily converted to nickel(II) or palladium( 1) complexes. Reactions with alkenes are synthetically less useful as the addition proceeds without any chiral induction at the newly formed stereocenters to yield inseparable mixtures of diastereomeric products. The molecular structures of chiral Z-ethylene-1,2-bisphosphine complexes and of a chiral N-heterocyclic chlorophosphine have been determined by single-crystal X-ray diffraction.
ISSN:0932-0776
1865-7117
DOI:10.5560/ZNB.2012-0177