Asymmetric Synthesis of Functionalized 1,2-Diphosphine via the Chemoselective Hydrophosphination of Coordinated Allylic Phosphines

Ester- and keto-functionalized allylic monophosphine palladium complexes containing ortho-metalated (R)-(1-(dimethylamino)ethyl)naphthalene as the chiral auxiliary were synthesized via a versatile one-pot process. Subsequent asymmetric hydrophosphination of the coordinated allylic substrates promote...

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Bibliographic Details
Published in:Organometallics 2009-02, Vol.28 (3), p.780-786
Main Authors: Yuan, Mingjun, Pullarkat, Sumod A, Ma, Mengtao, Zhang, Yi, Huang, Yinhua, Li, Yongxin, Goel, Akash, Leung, Pak-Hing
Format: Article
Language:English
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Summary:Ester- and keto-functionalized allylic monophosphine palladium complexes containing ortho-metalated (R)-(1-(dimethylamino)ethyl)naphthalene as the chiral auxiliary were synthesized via a versatile one-pot process. Subsequent asymmetric hydrophosphination of the coordinated allylic substrates promoted by the chiral auxiliary gave the corresponding functionalized chiral 1,2-bis(diphenylphosphino)ethane ligands in high yields under mild conditions. The coordination properties and absolute configurations of the resultant diphosphine ligands were established by single-crystal X-ray crystallography. The coordinated 1,2-diphosphine ligands could be subsequently liberated stereospecifically to yield enantiomerically pure functionalized diphosphines in high yields.
ISSN:0276-7333
1520-6041
DOI:10.1021/om8009188