Stereospecific cleavage of carbon‐phosphorus bonds: Stereochemical course of the phosphinoyl curtius (harger) reaction | Zendy

Denmark Scott E. | Zendy; Dorow Roberta L. | Zendy

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Stereospecific cleavage of carbon‐phosphorus bonds: Stereochemical course of the phosphinoyl curtius (harger) reaction

Author(s) -

Denmark Scott E.,

Dorow Roberta L.

Publication year - 2002

Publication title -

chirality

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.43

H-Index - 77

eISSN - 1520-636X

pISSN - 0899-0042

DOI - 10.1002/chir.10062

Subject(s) - chemistry , diastereomer , stereocenter , curtius rearrangement , stereospecificity , azide , walden inversion , enantiopure drug , asymmetric carbon , stereochemistry , medicinal chemistry , methanol , carbon fibers , nitrogen , organic chemistry , optically active , catalysis , enantioselective synthesis , materials science , composite number , composite material

The homochiral phosphinic azides ( R , R ) ‐ 1 and ( S , S )‐ 1 were prepared in enantiomerically pure form by resolution of diastereomeric phosphinamides derived from ( S )‐l‐phenylethylamine and ( R )‐phenylglycine. Irradiation of the azides in methanol induced a photo‐Curtius rearrangement to phosphonamidates in which the stereogenic carbon unit migrated to a nitrogen atom. Hydrolysis of the phosphonamidates produced 1‐phenylethylamine, which was 99.0% e.e. and of the same configuration as the carbon unit in the starting azide (99.0% retention). Chirality 14:241–257, 2002.© 2002 Wiley‐Liss, Inc.

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