R)-1-[(1R)-1-(Dicyclohexylphosphino) ethyl]-2-(diphenylphosphino)-ferrocene and (2S)-1-[(1R)-1-(Dicyclohexylphosphino) ethyl]-2-(diphenylphosphino)-ferrocene (Josiphos)

SL-J001-1 (R = Ph, R′ = Cy) [155806-35-2] (MW 594.54) InChI = 1S/C31H39P2.C5H5.Fe/c1-25(32(26-15-6-2-7-16-26)27-17-8-3-9-18-27)30-23-14-24-31(30)33(28-19-10-4-11-20-28)29-21-12-5-13-22-29;1-2-4-5-3-1;/h4-5,10-14,19-27H,2-3,6-9,15-18H2,1H3;1-5H;/t25-;;/m1../s1 InChIKey = HGTBZFMPHBAUCQ-KHZPMNTOSA-N SL-J001-2 (R = Ph, R′ = Cy) [162291-02-3] (MW 594.54) InChI = 1S/C31H39P2.C5H5.Fe/c1-25(32(26-15-6-2-7-16-26)27-17-8-3-9-18-27)30-23-14-24-31(30)33(28-19-10-4-11-20-28)29-21-12-5-13-22-29;1-2-4-5-3-1;/h4-5,10-14,19-27H,2-3,6-9,15-18H2,1H3;1-5H;/t25-;;/m0../s1 InChIKey = HGTBZFMPHBAUCQ-WLOLSGMKSA-N SL-J002-1 (R = Ph, R′ = t-Bu) [155830-69-6] (MW 542.46) InChI = 1S/C27H35P2.C5H5.Fe/c1-21(29(26(2,3)4)27(5,6)7)24-19-14-20-25(24)28(22-15-10-8-11-16-22)23-17-12-9-13-18-23;1-2-4-5-3-1;/h8-21H,1-7H3;1-5H;/t21-;;/m1../s1 InChIKey = STAGMXYQPGLLTD-GHVWMZMZSA-N SL-J002-2 (R = Ph, R′ = t-Bu) [277306-29-3] (MW 542.46) InChI = 1S/C27H35P2.C5H5.Fe/c1-21(29(26(2,3)4)27(5,6)7)24-19-14-20-25(24)28(22-15-10-8-11-16-22)23-17-12-9-13-18-23;1-2-4-5-3-1;/h8-21H,1-7H3;1-5H;/t21-;;/m0../s1 InChIKey = STAGMXYQPGLLTD-FGJQBABTSA-N SL-J003-1 (R = Cy, Cy) [167416-28-6] (MW 606.63) InChI = 1S/C31H51P2.C5H5.Fe/c1-25(32(26-15-6-2-7-16-26)27-17-8-3-9-18-27)30-23-14-24-31(30)33(28-19-10-4-11-20-28)29-21-12-5-13-22-29;1-2-4-5-3-1;/h14,23-29H,2-13,15-22H2,1H3;1-5H;/t25-;;/m1../s1 InChIKey = LVJMXQBMWBNENE-KHZPMNTOSA-N SL-J003-2 (R = Cy, Cy) [158923-07-0] (MW 606.63) InChI = 1S/C31H51P2.C5H5.Fe/c1-25(32(26-15-6-2-7-16-26)27-17-8-3-9-18-27)30-23-14-24-31(30)33(28-19-10-4-11-20-28)29-21-12-5-13-22-29;1-2-4-5-3-1;/h14,23-29H,2-13,15-22H2,1H3;1-5H;/t25-;;/m0../s1 InChIKey = LVJMXQBMWBNENE-WLOLSGMKSA-N SL-J004-1 (R = Cy, Ph) [158923-09-2] (MW 594.54) InChI = 1S/C31H39P2.C5H5.Fe/c1-25(32(26-15-6-2-7-16-26)27-17-8-3-9-18-27)30-23-14-24-31(30)33(28-19-10-4-11-20-28)29-21-12-5-13-22-29;1-2-4-5-3-1;/h2-3,6-9,14-18,23-25,28-29H,4-5,10-13,19-22H2,1H3;1-5H;/t25-;;/m1../s1 InChIKey = AWOOIDCKLIQAJV-KHZPMNTOSA-N SL-J004-2 (R = Cy, Ph) [162291-01-2] (MW 594.54) InChI = 1S/C31H39P2.C5H5.Fe/c1-25(32(26-15-6-2-7-16-26)27-17-8-3-9-18-27)30-23-14-24-31(30)33(28-19-10-4-11-20-28)29-21-12-5-13-22-29;1-2-4-5-3-1;/h2-3,6-9,14-18,23-25,28-29H,4-5,10-13,19-22H2,1H3;1-5H;/t25-;;/m0../s1 InChIKey = AWOOIDCKLIQAJV-WLOLSGMKSA-N SL-J005-1 (R = Ph 3,5-Xyl) [184095-69-0] (MW 638.55) InChI = 1S/C35H35P2.C5H5.Fe/c1-25-19-26(2)22-32(21-25)36(33-23-27(3)20-28(4)24-33)29(5)34-17-12-18-35(34)37(30-13-8-6-9-14-30)31-15-10-7-11-16-31;1-2-4-5-3-1;/h6-24,29H,1-5H3;1-5H;/t29-;;/m1../s1 InChIKey = VIWMSTLBMCHMGT-SYXKTQFYSA-N SL-J005-2 (R = Ph 3,5-Xyl) [223121-07-1] (MW 638.55) InChI = 1S/C35H35P2.C5H5.Fe/c1-25-19-26(2)22-32(21-25)36(33-23-27(3)20-28(4)24-33)29(5)34-17-12-18-35(34)37(30-13-8-6-9-14-30)31-15-10-7-11-16-31;1-2-4-5-3-1;/h6-24,29H,1-5H3;1-5H;/t29-;;/m0../s1 InChIKey = VIWMSTLBMCHMGT-UJXPALLWSA-N SL-J006-1 (R = 3,5-(CF3)2C6H3 Cy) [292638-88-1] (MW 866.53) InChI = 1S/C35H35F12P2.C5H5.Fe/c1-21(48(26-9-4-2-5-10-26)27-11-6-3-7-12-27)30-13-8-14-31(30)49(28-17-22(32(36,37)38)15-23(18-28)33(39,40)41)29-19-24(34(42,43)44)16-25(20-29)35(45,46)47;1-2-4-5-3-1;/h8,13-21,26-27H,2-7,9-12H2,1H3;1-5H;/t21-;;/m1../s1 InChIKey = QRWXESUNHGCSDF-GHVWMZMZSA-N SL-J006-2 (R = 3,5-(CF3)2C6H3 Cy) [849923-15-5] (MW 866.53) InChI = 1S/C35H35F12P2.C5H5.Fe/c1-21(48(26-9-4-2-5-10-26)27-11-6-3-7-12-27)30-13-8-14-31(30)49(28-17-22(32(36,37)38)15-23(18-28)33(39,40)41)29-19-24(34(42,43)44)16-25(20-29)35(45,46)47;1-2-4-5-3-1;/h8,13-21,26-27H,2-7,9-12H2,1H3;1-5H;/t21-;;/m0../s1 InChIKey = QRWXESUNHGCSDF-FGJQBABTSA-N SL-J007-1 (R = 4-MeO-Xyl Cy) [360048-63-1] (MW 710.71) InChI = 1S/C37H51O2P2.C5H5.Fe/c1-25-21-32(22-26(2)36(25)38-6)41(33-23-27(3)37(39-7)28(4)24-33)35-20-14-19-34(35)29(5)40(30-15-10-8-11-16-30)31-17-12-9-13-18-31;1-2-4-5-3-1;/h14,19-24,29-31H,8-13,15-18H2,1-7H3;1-5H;/t29-;;/m1../s1 InChIKey = QYTRSAIHSZHSTP-SYXKTQFYSA-N SL-J007-2 (R = 4-MeO-Xyl Cy) [849923-88-2] (MW 710.71) InChI = 1S/C37H51O2P2.C5H5.Fe/c1-25-21-32(22-26(2)36(25)38-6)41(33-23-27(3)37(39-7)28(4)24-33)35-20-14-19-34(35)29(5)40(30-15-10-8-11-16-30)31-17-12-9-13-18-31;1-2-4-5-3-1;/h14,19-24,29-31H,8-13,15-18H2,1-7H3;1-5H;/t29-;;/m0../s1 InChIKey = QYTRSAIHSZHSTP-UJXPALLWSA-N SL-J009-1 (R = Cy t-Bu) [158923-11-6] (MW 554.56) InChI = 1S/C27H47P2.C5H5.Fe/c1-21(29(26(2,3)4)27(5,6)7)24-19-14-20-25(24)28(22-15-10-8-11-16-22)23-17-12-9-13-18-23;1-2-4-5-3-1;/h14,19-23H,8-13,15-18H2,1-7H3;1-5H;/t21-;;/m1../s1 InChIKey = FFFWTQLOUUWUJJ-GHVWMZMZSA-N SL-J009-2 (R = Cy t-Bu) [194020-16-1] (MW 554.56) InChI = 1S/C27H47P2.C5H5.Fe/c1-21(29(26(2,3)4)27(5,6)7)24-19-14-20-25(24)28(22-15-10-8-11-16-22)23-17-12-9-13-18-23;1-2-4-5-3-1;/h14,19-23H,8-13,15-18H2,1-7H3;1-5H;/t21-;;/m0../s1 InChIKey = FFFWTQLOUUWUJJ-FGJQBABTSA-N SL-J011-1 (R = 4-CF3-C6H4 t-Bu) [246231-79-8] (MW 678.46) InChI = 1S/C29H33F6P2.C5H5.Fe/c1-19(37(26(2,3)4)27(5,6)7)24-9-8-10-25(24)36(22-15-11-20(12-16-22)28(30,31)32)23-17-13-21(14-18-23)29(33,34)35;1-2-4-5-3-1;/h8-19H,1-7H3;1-5H;/t19-;;/m1../s1 InChIKey = ZYPSDHCBNMCWCZ-JQDLGSOUSA-N SL-J011-2 (R = 4-CF3-C6H4 t-Bu) [849924-37-4] (MW 678.46) InChI = 1S/C29H33F6P2.C5H5.Fe/c1-19(37(26(2,3)4)27(5,6)7)24-9-8-10-25(24)36(22-15-11-20(12-16-22)28(30,31)32)23-17-13-21(14-18-23)29(33,34)35;1-2-4-5-3-1;/h8-19H,1-7H3;1-5H;/t19-;;/m0../s1 InChIKey = ZYPSDHCBNMCWCZ-TXEPZDRESA-N SL-J013-1 (R = 4-MeO-Xyl t-Bu) [187733-50-2] (MW 658.62) InChI = 1S/C33H47O2P2.C5H5.Fe/c1-21-17-26(18-22(2)30(21)34-12)36(27-19-23(3)31(35-13)24(4)20-27)29-16-14-15-28(29)25(5)37(32(6,7)8)33(9,10)11;1-2-4-5-3-1;/h14-20,25H,1-13H3;1-5H;/t25-;;/m1../s1 InChIKey = UALLLNAXGQTBJA-KHZPMNTOSA-N SL-J013-2 (R = 4-MeO-Xyl t-Bu) [849924-40-9] (MW 658.62) InChI = 1S/C33H47O2P2.C5H5.Fe/c1-21-17-26(18-22(2)30(21)34-12)36(27-19-23(3)31(35-13)24(4)20-27)29-16-14-15-28(29)25(5)37(32(6,7)8)33(9,10)11;1-2-4-5-3-1;/h14-20,25H,1-13H3;1-5H;/t25-;;/m0../s1 InChIKey = UALLLNAXGQTBJA-WLOLSGMKSA-N SL-J102-1 (R = Ph 3-Tolyl) [184095-68-9] (MW 610.51) InChI = 1S/C33H31P2.C5H5.Fe/c1-25-13-10-19-30(23-25)34(31-20-11-14-26(2)24-31)27(3)32-21-12-22-33(32)35(28-15-6-4-7-16-28)29-17-8-5-9-18-29;1-2-4-5-3-1;/h4-24,27H,1-3H3;1-5H;/t27-;;/m1../s1 InChIKey = KBWDVQCHDZQZQR-KFSCGDPASA-N SL-J102-2 (R = Ph 3-Tolyl) [−] (MW 610.51) SL-J106-1 (R = Ph 2-Anisyl) [155830-66-3] (MW 642.5) InChI = 1S/C33H31O2P2.C5H5.Fe/c1-25(36(32-22-12-10-20-29(32)34-2)33-23-13-11-21-30(33)35-3)28-19-14-24-31(28)37(26-15-6-4-7-16-26)27-17-8-5-9-18-27;1-2-4-5-3-1;/h4-25H,1-3H3;1-5H;/t25-;;/m1../s1 InChIKey = NLKOHBMYNYTBDD-KHZPMNTOSA-N SL-J106-2(R = Ph 2-Anisyl) [−] (MW 642.5) SL-J110-1 (R = Ph 4-CF3C6H4) [155830-73-2] (MW 718.45) InChI = 1S/C33H25F6P2.C5H5.Fe/c1-23(30-13-8-14-31(30)41(26-9-4-2-5-10-26)27-11-6-3-7-12-27)40(28-19-15-24(16-20-28)32(34,35)36)29-21-17-25(18-22-29)33(37,38)39;1-2-4-5-3-1;/h2-23H,1H3;1-5H;/t23-;;/m1../s1 InChIKey = UGZCNNVCASLGJU-MQWQBNKOSA-N SL-J110-2 (R = Ph 4-CF3C6H4) [−] (MW 718.45) SL-J408-1 (R = Xyl Xyl) [349150-76-1] (MW 694.67) InChI = 1S/C39H43P2.C5H5.Fe/c1-25-13-26(2)18-34(17-25)40(35-19-27(3)14-28(4)20-35)33(9)38-11-10-12-39(38)41(36-21-29(5)15-30(6)22-36)37-23-31(7)16-32(8)24-37;1-2-4-5-3-1;/h10-24,33H,1-9H3;1-5H;/t33-;;/m1../s1 InChIKey = QOUOHAFLPDJJLR-QYKZUBHNSA-N SL-J408-2 (R = Xyl Xyl) [158923-10-5] (MW 694.67) InChI = 1S/C39H43P2.C5H5.Fe/c1-25-13-26(2)18-34(17-25)40(35-19-27(3)14-28(4)20-35)33(9)38-11-10-12-39(38)41(36-21-29(5)15-30(6)22-36)37-23-31(7)16-32(8)24-37;1-2-4-5-3-1;/h10-24,33H,1-9H3;1-5H;/t33-;;/m0../s1 InChIKey = QOUOHAFLPDJJLR-NYPSMHOZSA-N (chiral diphosphine ligand for transition metals; the complexes show high enantioselectivity and reactivity in a variety of organic synthetic transformations)1, 2 Alternate Name: Josiphos. Physical Data: optical rotation values (c = 0.5, CHCl3) Solubility: well soluble in most organic solvents (such as diethyl ether, THF, CH2Cl2, etc.), partially soluble in alcohols (such as MeOH, EtOH, etc.), insoluble in water. Form Supplied in: orange or yellow solids. Purification: crystallization from EtOH or MeOH. Handling, Storage, and Precautions: air-stable in solid form in closed bottles over years. Josiphos is a family of diphosphines with the 1-(PR2)-2-(1-(PR′2)ethyl)-ferrocene scaffold, the substituents R and R′ at the P atoms encompassing phenyl, substituted phenyl, heteroaryl, alkyl, and cycloalkyl. Up to now, only the (R,SFc)-family (and its enantiomers) but not the (R,RFc)-diastereomers have led to high enantioselectivities. Some members of the family, that is, those referred to in the reactions below, are depicted with their numbering in the list above. In most case, the (R,SFc) enantiomers (numbering SL-Jxxx-1) have been used, but both enantiomers of all ligands are available from Aldrich and Strem, and for technical quantities from Solvias AG, Basel, Switzerland.