Achiral Aminophosphine Ligands
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![22, [1053657-14-9] M-15-0253 (2-ammonioethyl)diisopropylphosphonium bis(tetrafluoroborate), C 8H 22B 2F 8; F.W: 336.85; [1222630-50-3] M-15-0103 2-(Di-tert-butylphosphino)ethylamine, C 10H 24; F.](/docs-images/85/91517010/images/1-1.jpg "W: 189.28; [1053658-84-6] M-15-0255 (2-ammonioethyl)di-tert-butylphosphonium bis(tetrafluoroborate), C 10H 26B 2F 8; F.W: 363.")
1 AMËA COR Argentia Road, Suite 8-9, rcury Bioscience Centre, Mississauga, O L5 8G4, Canada Achiral Aminophosphine Ligands M (Diphenylphosphino)ethylamine, C 14H 16; F.W: ; [ ] M (diphenylphosphino)ethanaminium tetrafluoroborate, C 14H 17; F.W: ; [ ] M (Diisopropylphosphino)ethylamine, C 8H 20; F.W: , [ ] M (2-ammonioethyl)diisopropylphosphonium bis(tetrafluoroborate), C 8H 22B 2F 8; F.W: ; [ ] M (Di-tert-butylphosphino)ethylamine, C 10H 24; F.W: ; [ ] M (2-ammonioethyl)di-tert-butylphosphonium bis(tetrafluoroborate), C 10H 26B 2F 8; F.W: ; [ ] M (Diphenylphosphino)propylamine, C 15H 18; F.W: ; [ ] M (diphenylphosphino)propan-1-aminium tetrafluoroborate, C 15H 19; F.W: M (Diisopropylphosphino)propylamine, C 9H 22; F.W: ; [ ] M (3-ammoniopropyl)diisopropylphosphonium bis(tetrafluoroborate), C 9H 24B 2F 8; F.W: M (Di-tert-butylphosphino)propylamine, C 11H 26; F.W: ; [ ] M (3-ammoniopropyl)di-tert-butylphosphonium bis(tetrafluoroborate), C 11H 27B 2F 8; F.W: Chiral Aminophosphine Ligands h 2 M (-)-(R)-2-(diphenylphosphino)-1-phenylethanamine, C 26H 24; F.W: ; [ ] h 2 H 3 M (R)-2-(diphenylphosphino)-1-phenylethanaminium tetrafluoroborate, C 20H 21; F.W: h 2 M (+)-(S)-2-(diphenylphosphino)-1-phenylethanamine, C 26H 24; F.W: ; [ ] h 2 H 3 M (S)-2-(diphenylphosphino)-1-phenylethanaminium tetrafluoroborate, C 20H 21; F.W: h 2 M (R)-1-(diphenylphosphino)-3-methylbutan-2- amine, C 17H 22; F.W: ; [ ] h 2 H 3 M (R)-1-(diphenylphosphino)-3-methylbutan- 2-aminium tetrafluoroborate, C 17H 23; F.W:
2 AMËA COR Argentia Road, Suite 8-9, rcury Bioscience Centre, Mississauga, O L5 8G4, Canada h 2 M (S)-1-(diphenylphosphino)-3-methylbutan-2- amine, C 17H 22; F.W: ; [ ] h 2 H 3 M (S)-1-(diphenylphosphino)-3-methylbutan- 2-aminium tetrafluoroborate, C 17H 23; F.W: M (R)-1-(diphenylphosphino)-3,3-dimethylbutan-2-amine, C 18H 24; F.W: ; [ ] M (R)-1-(diphenylphosphino)-3,3-dimethylbutan-2-aminium tetrafluoroborate, C 18H 25; F.W: M (S)-1-(diphenylphosphino)-3,3-dimethylbutan-2-amine, C 18H 24; F.W: ; [ ] M (S)-1-(diphenylphosphino)-3,3-dimethylbutan-2-aminium tetrafluoroborate, C 18H 25; F.W: h 2 M (R)-1-(2-(diphenylphosphino)phenyl)ethanamine, C 20H 20; F.W: ; [ ] M (S)-1-(2-(diphenylphosphino)phenyl) ethana-mine, C 20H 20; F.W: ; [ ] h 2 M (R)-8-(diphenylphosphino)-1,2,3,4- tetrahydronaphthalen-1-amine, C 22H 22; F.W: ; [ ] M (R)-8-(diphenylphosphino)-1,2,3,4- tetrahydronaphthalen-1-aminium tetrafluoroborate, C 22H 23; F.W: ; [ ] M (S)-8-(diphenylphosphino)-1,2,3,4- tetrahydronaphthalen-1-amine, C 22H 22; F.W: ; [ ] M (S)-8-(diphenylphosphino)-1,2,3,4- tetrahydronaphthalen-1-aminium tetrafluoroborate, C 22H 23; F.W: ; [ ] H h 2 M (R)-2-((diphenylphosphino)methyl)- pyrrolidine, C 17H 20; F.W: ; [ ] M (R)-2-((diphenylphosphino)methyl)- pyrrolidinium tetrafluoroborate, C 17H 21; F.W: M (S)-2-((diphenylphosphino)methyl)- pyrrolidine, C 17H 20; F.W: ; [ ] M (S)-2-((diphenylphosphino)methyl)- pyrrolidinium tetrafluoroborate, C 17H 21; F.W: ; [ ] M (-)-2-((11bR)-3H-Binaphtho[2,1-c:1',2'-e]- phosphepin-4(5h)-yl)ethanamine, C 24H 22; F.W: ; [ ] H 3 M ((11bR)-3H-dinaphtho[2,1-c:1',2'- e]phosphepin-4(5h)-yl)ethanaminium tetrafluoroborate, C 24H 23; F.W:
3 AMËA COR Argentia Road, Suite 8-9, rcury Bioscience Centre, Mississauga, O L5 8G4, Canada M (+)-2-((11bS)-3H-Binaphtho[2,1-c:1',2'-e]- phosphepin-4(5h)-yl)ethanamine, C 24H 22; F.W: ; [ ] H 3 M ((11bS)-3H-dinaphtho[2,1-c:1',2'- e]phosphepin-4(5h)-yl)ethanaminium tetrafluoroborate, C 24H 23; F.W: ; [ ] h 2 M (-)-(1R,2R)-2-Amino-1-phenylpropyldiphenylphosphine, C 21H 22; F.W: ; [ ] M (1R,2R)-1-(diphenylphosphino)-1-phenylpropan-2-aminium tetrafluoroborate, C 21H 23; F.W: h 2 M (+)-(1S,2S)-2-Amino-1-phenylpropyldiphenylphosphine, C 21H 22; F.W: ; [ ] M (1S,2S)-1-(diphenylphosphino)-1-phenylpropan-2-aminium tetrafluoroborate, C 21H 23; F.W: ; [ ] h 2 M (1R,2R)-2-(Diphenylphosphino)-1,2- diphenylethylamine, C 26H 24; F.W: ; [ ] M (1R,2R)-2-(diphenylphosphino)-1,2- C 26H 25; F.W: ; [ ] h 2 M (1S,2S)-2-(Diphenylphosphino)-1,2- diphenylethylamine, C 26H 24; F.W: ; [ ] M (1S,2S)-2-(diphenylphosphino)-1,2- C 26H 25; F.W: ; [ ] M (1R,2R)-2-(diphenylphosphino)-2,3-dihydro- 1H-inden-1-amine, C 21H 20; F.W: ; [ ] M (1R,2R)-2-(diphenylphosphino)-2,3-dihydro- 1H-inden-1-aminium tetrafluoroborate, C 21H 21; F.W: ; [ ] h 2 M (1S,2S)-2-(diphenylphosphino)-2,3-dihydro- 1H-inden-1-amine, C 21H 20; F.W: ; [ ] M (1S,2S)-2-(diphenylphosphino)-2,3-dihydro- 1H-inden-1-aminium tetrafluoroborate, C 21H 21; F.W: ; [ ] M (1R,2R)-2-(diphenylphosphino)cyclohexanamine, C 18H 22; F.W: ; [ ] M (1R,2R)-2- (diphenylphosphino)cyclohexanaminium tetrafluoroborate, C 18H 23; F.W: M (1S,2S)-2-(diphenylphosphino)cyclohexanamine, C 18H 22; F.W: ; [ ] M (1S,2S)-2- (diphenylphosphino)cyclohexanaminium tetrafluoroborate, C 18H 23; F.W:
4 AMËA COR Argentia Road, Suite 8-9, rcury Bioscience Centre, Mississauga, O L5 8G4, Canada M (R)-1-((S)-2-Diphenylphosphino)ferrocenylethylamine, C 24H 24; F.W: h 2 M (S)-1-((R)-2-Diphenylphosphino)ferrocenylethylamine, C 24H 24; F.W: ; [ ] M (+)-(1S,2S)-2-((4R,11bS)-3H-dinaphtho[2,1- diphenylethanamine, C 36H 30; F.W: ; [ ] H 3 M (1S,2S)-2-((4R,11bS)-3H-dinaphtho[2,1- C 36H 31; F.W: ; [ ] H 2 M (-)-(1R,2R)-2-((4S,11bR)-3H-dinaphtho[2,1- diphenylethanamine, C 36H 30; F.W: ; [ ] H 3 M (1R,2R)-2-((4S,11bR)-3H-dinaphtho[2,1- C 36H 31; F.W: M (1S,2S)-1-((4R,11bS)-3H-dinaphtho[2,1- phenylpropan-2-amine, C 31H 28; F.W: ; [ ] H 3 M (1S,2S)-1-((4R,11bS)-3H-dinaphtho[2,1- phenylpropan-2-aminium tetrafluoroborate, C 31H 29; F.W: ; [ ] M (1R,2R)-1-((4S,11bR)-3H-dinaphtho[2,1- phenylpropan-2-amine, C 31H 28; F.W: H 3 M (1R,2R)-1-((4S,11bR)-3H-dinaphtho[2,1- phenylpropan-2-aminium tetrafluoroborate, C 31H 29; F.W:
5 AMËA COR Argentia Road, Suite 8-9, rcury Bioscience Centre, Mississauga, O L5 8G4, Canada Aminophosphines represent a new class of "privileged" ligands for asymmetric catalysis. They exhibit high performance in a large array of catalytic transformations such as hydrogenation, 1 Michael addition, 2 the addition of organolithium reagents to aldehydes, 3 allylic alkylation, 4 hydroformylation 5 and cycloaddition reactions. 6 AMËA Chemicals offers a leading portfolio of chiral and achiral aminophosphines and their corresponding quaternary aminophosphine salts which offer increased air-stability and shelf-life. ertinent examples are depicted in reactions 1-4. reparation of Ru Aminophosphine Catalyst: [RuCl 2 (COD)] n + H h 2 3 BF Et 3 toluene, h 2 H 2 Cl Ru Cl h 2 H2 Asymmetric Hydrogenation of tert-butylcyclohexanone: 1a O ir 2 Ru H 2 Cl ir 2 H2 OH H 2 /Base 98% d.e. Intermediate f or W oody Acetate Enantioselective [2+2] Cycloaddition: 6 CO 2 Et h 2 O 2 C CO 2 CO 2 + CO 2 4-Cl-C 6 H 4 H 4-Cl-C 6 H 4 CO 2 Et AgOAc H 83% e.e. Bohoz Ligands in Asymmetric Rh-Catalyzed Hydrogenation: 1b h 2 h 2 Bohoz H h 2 R HR' CO 2 R' [Rh(COD) 2 ]OTf/Bohoz H 2 R H > 99.5% References 1. (a) Chen, X. et al. US atent Appl. 60/948, 238, (b) Boaz,. W. et al. Org. Lett. 2002, 4, Guo, R. et al. J. Am. Chem. Soc. 2005, 127, Rönnholm,. et al. Org. Lett. 2007, 9, Saitoh, A. et al. Tetrahedron Asymmetry 1997, 8, Andrieu, J. et al. Eur. J. Inorg. Chem. 2006, Zeng, W. et al. J. Am. Chem. Soc. 2007, 129, 750.
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