Solvias (R)-MeO-BIPHEP Ligand Kit
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1 metals inorganics organometallics catalysts ligands custom synthesis cgm facilities nanomaterials Catalog # Solvias ()- and (S)-Me BIE Ligand Kits for asymmetric hydrogenation and other catalytic applications Solvias ()-Me-BIE Ligand Kit Components include of the nine items listed below: Cat. # Cat. # Cat. # C 3 C 3 C 3 C 3 C 3 C Cat. # Cat. # Cat. # C 3 C 3 C 3 C 3 C 3 C Cat. # Cat.# Cat.# C(C 3 ) N(C 3 ) 3 C 3 C 3 C C(C 3 ) 3 C 3 C 3 C C(C 3 ) N(C 3 ) C(C 3 ) Solvias (S)-Me-BIE Ligand Kit - components include of the nine S-enantiomers of the ligands contained in the ()-Kit (# ) above ()-(+)-,'-Bis(diphenylphosphino)-6,6'-dimethoxy-1,1'-biphenyl, min. 97% ()-Me-BIE [ ] C 38 3 ; FW: 58.53; off-white xtl. 1 kit g Technical Notes: In many respects the catalytic profile of the MeBIE ligands is similar to that of other atropisomeric diphosphines such as binap and its many analogs. The nature of the group strongly influences the catalytic performance of the metal complexes. The rhodium and ruthenium Me- BIE catalysts are highly effective for the hydrogenation of various C=, C=C and C=N bonds and several synthetically useful CC coupling reactions. 1. u catalyzed asymmetric hydrogenation of $-keto esters, $-keto sulfones and "-keto amides.. u and Ir catalyzed dynamic kinetic resolution for the synthesis of $-hydroxy-"-amino acid derivatives. 3. u catalyzed hydrogenation of C=C bonds, especially ",$-unsaturated acids, allylic alcohols and with other activated groups. 4. Ir catalyzed enantioselective hydrogenation of heteroaromatic compounds. 5. Various asymmetric C-C coupling reactions such as h catalyzed reductive coupling of acetylene to aldehydes and "-ketoesters, t catalyzed intramolecular hydroarylation of unactivated alkenes with indoles and glyoxylate-ene reaction or the d catalyzed enantioselective eck reaction of p-xc64tf (X = Me,, CMe) with dihydrofuran. Solvias_Me-BIE011 Tel.: (33) Fax: (33) ostfach KEL England CB 1NT Tel.: Fax:
2 -- X = alkyl, (subst) h, Np X = C', S h u - MeBIE 1-10 bar, C X 88-97% ee Tech. Note (1) ef. (1-3) Cl N [u(p-cymene)i ] ()-MeBIE s/c 4000, 0 h Me, 1 N Cl 80 bar, 60 C Cl 90-93% ee N Tech. Note (1) ef. (4) CMe N. Cl 1) [Ir-MeBIE]BAF Ac / NaAc ) Bz, TEA, TF CMe NBz 9% ee, dr >99 Tech. Note () ef. (5) C u - MeBIE s/c ~80, 4 h Me / NEt bar, 0 C C 100% conv., 98% ee Tech. Note (3) ef. (6-9) Me tbuc u / MeBIE 50 C, 9 bar Me CNaee 99%; ton 1'000; tof 300h -1 tbuc pilot process, G-Sipsy CNa Tech. Note (3) ef. (10) ' N = (subst) alkyl ' =, F, Me, Me [Ir(cod) Cl] / MeBIE s/c 100, 18 h toluene, I 50 bar, 5 C ' N y 80-99%, 86-96% ee Tech. Note 4) ef. (11) + ' h - MeBIE DCE, h 3 CC, Na S 4 eferences: 1 bar, 5 C 1. Adv. Synth. Catal. 003, 345, 61.. J. rganomet. Chem. 000, 603, Tetrahedron: Asymmetry 1999, 10, Adv. Synth. Catal. 004, 346, rg. Lett. 006, 8, Tetrahedron Lett. 006, 47, Comprehensive Asymmetric Catalysis, 1999, Chimia 1997, 51, J. Am. Chem. Soc. 003, 15, rg. rocess es. Devel. 001, 5, J. Am. Chem. Soc. 003, 15, J. Am. Chem. Soc. 006, 18, ' y ~80%, ee 89% Tech. Note (5) ef. (1) Solvias_Me-BIE011 Tel.: (33) Fax: (33) ostfach KEL England CB 1NT Tel.: Fax:
3 ()-(-)-,'-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C ; FW: ; white xtl. g 1. Various asymmetric C-C coupling reactions such as h catalyzed reductive coupling of acetylene to aldehydes and "-ketoesters, t catalyzed intramolecular hydroarylation of unactivated alkenes with indoles and glyoxylate-ene reaction or the d catalyzed enantioselective eck reaction of p-xc64tf (X = Me,, CMe) with dihydrofuran.. See " N t(3.5-tbu -4-Me-h-MeBIE)Cl ' AgTf ' Me, 5 C eference: 56-96%, ee up to 90% 1. rg. Lett. 006, 8, ()-(+)-,'-Bis(di--furanylphosphino)-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C ; FW: 54.47; off-white pwdr ()-(+)-,'-Bis[di(3,5-xylyl)phosphino]-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C ; FW: ; white pwdr ()-(+)-,'-Bis(di-i-propylphosphino)-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C 6 40 ; FW: ; white pwdr ()-(+)-,'-Bis(di-p-tolylphosphino)-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C 4 40 ; FW: ; white pwdr ()-(+)-,'-Bis[di(3,5-di-t-butylphenyl)phosphino]-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C ; FW: ; white pwdr. " N ' ' g g g g g Technical Notes: 1. Various asymmetric C-C coupling reactions such as h catalyzed reductive coupling of acetylene to aldehydes and "-ketoesters, t catalyzed intramolecular hydroarylation of unactivated alkenes with indoles and glyoxylate-ene reaction or the d catalyzed enantioselective eck reaction of p-xc64tf (X = Me,, CMe) with dihydrofuran.. See Tf + =, Me eference: 1. rganometallics 1999, 18, 670. d - (3,5-tBu -h-mebie) acetone, 40 C NEt(i-r) ee >98% + isomer Solvias_Me-BIE011 Tel.: (33) Fax: (33) ostfach KEL England CB 1NT Tel.: Fax:
4 ()-(+)-,'-Bis[di(3,4,5-trimethoxyphenyl)phosphino]-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C ; FW: 94.94; off-white pwdr ()-(-)-,'-Bis[di(3,5-di-i-propyl-4-dimethylaminophenyl)phosphino]-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C N 4 ; FW: ; white pwdr. (S)-enantiomers listed below (S)-(-)-,'-Bis(diphenylphosphino)-6,6'-dimethoxy-1,1'-biphenYyl, min. 97% (S)-Me-BIE [ ] C 38 3 ; FW: 58.53; white xtl S)-(+)-,'-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C ; FW: ; white xtl. 1. See (S)-(-)-,'-Bis(di--furanylphosphino)-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C ; FW: 54.47; off-white pwdr. g g g g g (S)-(-)-,'-Bis[di(3,5-xylyl)phosphino]-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C ; FW: ; white pwdr (S)-(-)-,'-Bis(di-i-propylphosphino)-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C 6 40 ; FW: ; white pwdr (S)-(-)-,'-Bis(di-p-tolylphosphino)-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C 4 40 ; FW: ; white pwdr (S)-(-)-,'-Bis[di(3,5-di-t-butylphenyl)phosphino]-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C ; FW: ; white pwdr. 1. See g g g g Solvias_Me-BIE011 Tel.: (33) Fax: (33) ostfach KEL England CB 1NT Tel.: Fax:
5 (S)-(-)-,'-Bis[di(3,4,5-trimethoxyphenyl)phosphino]-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C ; FW: 94.94; off-white pwdr (S)-(+)-,'-Bis[di(3,5-di-i-propyl-4-dimethylaminophenyl)phosphino]-6,6'-dimethoxy-1,1'-biphenyl, min. 97% [ ] C N 4 ; FW: ; white pwdr. g g Solvias_Me-BIE011 Tel.: (33) Fax: (33) ostfach KEL England CB 1NT Tel.: Fax:
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