Synthesis of 1,1′-binaphthyl-2,2′-diyl phosphoroselenoic amides and their conversion to optically pure phosphoramidites

Toshiaki Murai; Shinsuke Inaji; Ken Morishita; Fumitoshi Shibahara; Makoto Tokunaga; Yasushi Obora; Yasushi Tsuji

doi:10.1246/cl.2006.1424

Synthesis of 1,1′-binaphthyl-2,2′-diyl phosphoroselenoic amides and their conversion to optically pure phosphoramidites

Toshiaki Murai, Shinsuke Inaji, Ken Morishita, Fumitoshi Shibahara, Makoto Tokunaga, Yasushi Obora, Yasushi Tsuji

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

Optically pure phosphoroselenoyl chloride was reacted with racemic amines to give phosphoroselenoic amides as two diastereomeric mixtures in high yields. The diastereomeric mixtures were separated by fractional recrystallization or by chromatography. Extrusion of the selenium atom from the separated amides led to diastereomerically pure phosphoramidites. The ability of the obtained amidites to act as optically active ligands was tested in the hydrogenation of an imine.

Original language	English
Pages (from-to)	1424-1425
Number of pages	2
Journal	Chemistry Letters
Volume	35
Issue number	12
DOIs	https://doi.org/10.1246/cl.2006.1424
Publication status	Published - Dec 5 2006
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1246/cl.2006.1424

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title = "Synthesis of 1,1′-binaphthyl-2,2′-diyl phosphoroselenoic amides and their conversion to optically pure phosphoramidites",

abstract = "Optically pure phosphoroselenoyl chloride was reacted with racemic amines to give phosphoroselenoic amides as two diastereomeric mixtures in high yields. The diastereomeric mixtures were separated by fractional recrystallization or by chromatography. Extrusion of the selenium atom from the separated amides led to diastereomerically pure phosphoramidites. The ability of the obtained amidites to act as optically active ligands was tested in the hydrogenation of an imine.",

author = "Toshiaki Murai and Shinsuke Inaji and Ken Morishita and Fumitoshi Shibahara and Makoto Tokunaga and Yasushi Obora and Yasushi Tsuji",

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language = "English",

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T1 - Synthesis of 1,1′-binaphthyl-2,2′-diyl phosphoroselenoic amides and their conversion to optically pure phosphoramidites

AU - Murai, Toshiaki

AU - Inaji, Shinsuke

AU - Morishita, Ken

AU - Shibahara, Fumitoshi

AU - Tokunaga, Makoto

AU - Obora, Yasushi

AU - Tsuji, Yasushi

PY - 2006/12/5

Y1 - 2006/12/5

N2 - Optically pure phosphoroselenoyl chloride was reacted with racemic amines to give phosphoroselenoic amides as two diastereomeric mixtures in high yields. The diastereomeric mixtures were separated by fractional recrystallization or by chromatography. Extrusion of the selenium atom from the separated amides led to diastereomerically pure phosphoramidites. The ability of the obtained amidites to act as optically active ligands was tested in the hydrogenation of an imine.

AB - Optically pure phosphoroselenoyl chloride was reacted with racemic amines to give phosphoroselenoic amides as two diastereomeric mixtures in high yields. The diastereomeric mixtures were separated by fractional recrystallization or by chromatography. Extrusion of the selenium atom from the separated amides led to diastereomerically pure phosphoramidites. The ability of the obtained amidites to act as optically active ligands was tested in the hydrogenation of an imine.

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JO - Chemistry Letters

JF - Chemistry Letters

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ER -

Synthesis of 1,1′-binaphthyl-2,2′-diyl phosphoroselenoic amides and their conversion to optically pure phosphoramidites

Abstract

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