Molecular Recognition in a Palladium Complex Promoted Asymmetric Synthesis of a P-Chiral Heterodifunctionalized Bidentate Phosphine Ligand

The organopalladium complex containing orthometalated (S)-(1-(dimethylamino)ethyl)naphthalene as the chiral auxiliary has been used successfully to promote the asymmetric [4+2] Diels−Alder reaction between 3,4-dimethyl-1-phenylphosphole and 2-methylene-3-quinuclidinone. In this reaction, the organop...

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Bibliographic Details
Published in:Organometallics 1999-02, Vol.18 (4), p.650-655
Main Authors: Song, Yongcheng, Vittal, Jagadese J, Chan, Soh-Ha, Leung, Pak-Hing
Format: Article
Language:English
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Summary:The organopalladium complex containing orthometalated (S)-(1-(dimethylamino)ethyl)naphthalene as the chiral auxiliary has been used successfully to promote the asymmetric [4+2] Diels−Alder reaction between 3,4-dimethyl-1-phenylphosphole and 2-methylene-3-quinuclidinone. In this reaction, the organopalladium template exhibited remarkable stereochemical and electronic directing effects such that the quinuclidinone-nitrogen atom in the resulting phosphanorbornene cycloadduct is located stereospecifically in the exo position. Only one enantiomerically pure P−N bidentate ligand was obtained, although four diastereomeric products are possible. The absolute configuration and the coordination properties of the P-chiral cycloadduct have been established by single-crystal X-ray analyses.
ISSN:0276-7333
1520-6041
DOI:10.1021/om980776x