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Chiral bis-phospholanes are playing an important role in the development of enantioselective hydrogenation

Asymmetric hydrogenation transformations are among the most powerful and straightforward processes for delivering enantiomeric pure compounds. In the early 1990’s, Burk and colleagues achieved significant progress in this regard by introducing a new class of highly effective chiral phosphine ligands derived from 1,2-bis(2,5-dialkylphospholano)ethane (BPE) and 1,2-bis(2,5-dialkylphospholano)benzene (DuPHOS) [1,2]. These ligands feature a 2,5-disubstituted phospholane unit linked either with benzene (DuPhos ligands) or an ethylene bridge (BPE ligands).

96-4730 (R,R)-Duphos and BPE Rhodium Catalyst Kit for Asymmetric Hydrogenation

96-4731 (S,S)-Duphos and BPE Rhodium Catalyst Kit for Asymmetric Hydrogenation

The invention of these ligands has considerably expanded the substrate scope of Rh-catalyzed enantioselective hydrogenation [3].  Furthermore, the combination of robustness, high activity, and excellent selectivity, makes these ligands suitable for largescale industrial application. The ever-growing number of structural analogues reported in the literature confirms the practicality of phospholane ligands. For example, some research groups reported a series of modified DuPhos and BPE ligands with ether, ketal, or hydroxyl groups at the 3 and 4 positions of the phospholanes. These types of ligands maintain the high efficiency of DuPhos or BPE in Rh-catalyzed hydrogenation [4-6].

Recent achievements in asymmetric hydrogenation involves earth-abundant cobalt instead of costly rhodium [7]. This makes bis-phospholane ligands even more attractive. A variety of cobalt precursors generate highly active catalysts for selective asymmetric hydrogenation of both functionalized and un-functionalized alkenes [7].

Co-phospholane catalyzed asymmetric hydrogenation

DuPhos and BPE ligands are able to solve many challenging problems of asymmetric hydrogenation, providing excellent enantioselectivity for a variety of substrates. For more detailed information, please review DuPhos™ and BPE Technology product sheet and our family of Rh-phospholane catalysts with corresponding technical notes.

References:

1. Science 1993, 259, 479.
2.  Acc. Chem. Res. 2000, 33, 363.
3.  Chem. Rev. 2003, 103, 3029.
4. Eur. J. Org. Chem. 2001, 4615.
5. J. Org. Chem. 2000, 65, 3489.
6. J. Am. Chem. Soc. 2001, 123, 10207.
7. Science 2013, 342, 1076.

 Featured Products:

15-0097  (-)-1,2-Bis((2R,5R)-2,5-diethylphospholano)benzene, 98+% (R,R)-Et-DUPHOS (136705-64-1)   

15-0098 (+)-1,2-Bis((2S,5S)-2,5-diethylphospholano)benzene, 98+% (S,S)-Et-DUPHOS (136779-28-7)

15-0096 (-)-1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene, min.97% (R,R)-Me-DUPHOS (147253-67-6)

15-0092 (+)-1,2-Bis((2S,5S)-2,5-dimethylphospholano)benzene, 98+% (S,S)-Me-DUPHOS (136735-95-0)

15-0410 N,N-Bis(diphenylphosphino)amine, min. 98% (2960-37-4)            

15-0411 (-)-1,2-Bis((2S,5S)-2,5-di-i-propylphospholano)benzene, 98+% (S,S)-i-Pr-DUPHOS (147253-69-8)

15-0101 (+)-1,2-Bis((2R,5R)-2,5-diethylphospholano)ethane, 98+% (R,R)-Et-BPE (136705-62-9)

15-0102 (-)-1,2-Bis((2S,5S)-2,5-diethylphospholano)ethane, 98+% (S,S)-Et-BPE (136779-27-6)

15-0104  (+)-1,2-Bis((2R,5R)-2,5-dimethylphospholano)ethane, 98+% (R,R)-Me-BPE (129648-07-3)

15-0105 (-)-1,2-Bis((2S,5S)-2,5-dimethylphospholano)ethane, 98+% (S,S)-Me-BPE (136779-26-5)

15-0473 (-)-1,2-Bis((2R,5R)-2,5-diphenylphospholano)ethane, min. 95% (R,R)-Ph-BPE (528565-79-9)

15-0474 (+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane, min. 98% (S,S)-Ph-BPE (824395-67-7)

15-7357 1,2-Bis((2R,5R)-2,5-di-i-propylphospholano)ethane, 96% (136705-63-0)

15-7358 1,2-Bis((2S,5S)-2,5-di-i-propylphospholano)ethane, min. 97% (528854-34-4)

96-4730 (R,R)-Duphos and BPE Rhodium Catalyst Kit for Asymmetric Hydrogenation

96-4731 (S,S)-Duphos and BPE Rhodium Catalyst Kit for Asymmetric Hydrogenation

Related Product Lines:

BPE

Catalysts & Chiral Catalysts

DUPHOS

Ligands & Chiral Ligands

Phosphine