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  • Highly active, regioselective, and enantioselective hydroformylation with Rh catalysts ligated by Bis-3,4-diazaphospholanes.

Highly active, regioselective, and enantioselective hydroformylation with Rh catalysts ligated by Bis-3,4-diazaphospholanes.

Journal of the American Chemical Society (2005-04-07)
Thomas P Clark, Clark R Landis, Susan L Freed, Jerzy Klosin, Khalil A Abboud
摘要

Azines made by the reaction of hydrazine with ortho-formylbenzoic acid react with 1,2-diphosphinobenzene and either succinyl chloride or phthaloyl chloride in ca. 30% yield to give rac-bis-3,4-diazaphospholanes bearing benzoic acid groups in the 2 and 5 positions. Condensation of the benzoic acid functionalities with enantiomerically pure amines affords diastereomeric benzoamides which can be separated by flash chromatography. Application of the resolved bis-3,4-diazaphosholanes to Rh-catalyzed enantioselective hydroformylation of styrene, allyl cyanide, and vinyl acetate under mild pressures (20-500 psig of CO/H2) and temperatures (40-120 degrees C) reveals high activities and selectivities for all three substrates. At 60 degrees C and 500 psig syn gas, the best ligand provides outstanding regio- and enantioselectivities (styrene, 89% ee, b:l = 30:1; allyl cyanide, 87% ee, b:l = 4.8:1; vinyl acetate, 95% ee, b:l = 40:1) while achieving turnover frequencies of ca. 3000 h-1.

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Sigma-Aldrich
2,2′-[(1R,3R)-2,3,5,10-四氢-5,10-二氧-2-苯基-1H-[1,2,4]二氮杂磷杂环戊烷[1,2-b]酞嗪-1,3-二基]双[N-[(1S)-1-苯乙基]苯甲酰胺]
Sigma-Aldrich
2,2′-[(1S,3S)-2,3,5,10-四氢-5,10-二氧-2-苯基-1H-[1,2,4]二氮杂磷杂环戊烷[1,2-b]酞嗪-1,3-二基]双[N-(1S)-1-苯乙基]苯酰胺]

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