(2R,2′R, 5R,5′R)-1,1′-(1,2-Ethanediyl)bis[2,5-dimethylphospholane]; (2R,2′R, 5R,5′R)-1,1′-(1,2-ethanediyl)bis[2,5-diethylphospholane]; (2S,2′S, 5S,5′S)-1,1′-(1,2-ethanediyl)bis[2,5-di(2-propyl)phospholane] and (2S,2′S, 5S,5′S)-1,1′-(1,2-ethanediyl)bis[2,5

Abstract

(2R,2′R, 5R,5′R)-1,1′-(1,2-Ethanediyl)bis[2,5-dimethylphospholane][(R,R)-Me-BPE, 1a] [129648-07-3] C14H28P2 (MW 258.32) InChI = 1S/C14H28P2/c1-11-5-6-12(2)15(11)9-10-16-13(3)7-8-14(16)4/h11-14H,5-10H2,1-4H3/t11-,12-,13-,14-/m1/s1 InChIKey = IRCDUOCGSIGEAI-AAVRWANBSA-N Physical Data: bp 64–67 °C/0.06 mmHg. α D 25 + 279 ± 3 (c 1, hexane). Solubility: sol in pentane, ether, tetrahydrofuran, toluene. Form supplied in: colorless oil. Purification: obtained from synthesis as a yellow oil that can be used directly. Analytical samples can be obtained by distillation under high vacuum to afford the product as a colorless oil. Handling, Storage, and Precautions: the ligand should be stored in a tightly sealed container under an inert atmosphere. Prolonged exposure to the atmosphere will cause degradation, as with many other trialkylphosphines. As with other phosphines, these may cause skin and eye irritation, and may be harmful if ingested or inhaled. (2R,2′R, 5R,5′R)-1,1′-(1,2-Ethanediyl)bis[2,5-diethylphospholane] [(R,R)-Et-BPE, 1b] [136705-62-9] C18H36P2 (MW 314.43) InChI = 1S/C18H36P2/c1-5-15-9-10-16(6-2)19(15)13-14-20-17(7-3)11-12-18(20)8-4/h15-18H,5-14H2,1-4H3/t15-,16-,17-,18-/m1/s1 InChIKey = QOLRLVPABLMMKI-BRSBDYLESA-N Physical Data: bp 104–106 °C/0.05 mmHg. α D 25 + 320 ± 4 ° (c 1, hexane). Solubility: sol in pentane, ether, tetrahydrofuran, toluene, methanol, ethanol. Form supplied in: colorless oil. Purification: obtained from synthesis as a colorless oil that can be used directly. Analytical samples can be obtained by distillation under high vacuum. Handling, Storage, and Precautions: the ligand should be stored in a tightly sealed container under an inert atmosphere. Prolonged exposure to the atmosphere will cause degradation, as with many other trialkylphosphines. As with other phosphines, these may cause skin and eye irritation, and may be harmful if ingested or inhaled. (2S,2′S, 5S,5′(S)-1,1′-(1,2-Ethanediyl)bis[2,5-di(2-propyl)phospholane] [(S,S)-i-Pr-BPE, 1c] [136705-63-0] C22H44P2 (MW 370.53) InChI = 1S/C22H44P2/c1-15(2)19-9-10-20(16(3)4)23(19)13-14-24-21(17(5)6)11-12-22(24)18(7)8/h15-22H,9-14H2,1-8H3/t19-,20-,21-,22-/m0/s1 InChIKey = IRVIFEWWPYKALC-CMOCDZPBSA-N (2S,2′S, 5S,5′S)-1,1′-(1,2-Ethanediyl)bis[2,5-dimethylphospholane][(S,S)-Me-BPE, 2a] [136779-26-5] C14H28P2 (MW 258.32) InChI = 1S/C14H28P2/c1-11-5-6-12(2)15(11)9-10-16-13(3)7-8-14(16)4/h11-14H,5-10H2,1-4H3/t11-,12-,13-,14-/m0/s1 InChIKey = IRCDUOCGSIGEAI-XUXIUFHCSA-N (2S,2′S,5S,5′S)-1,1′-(1,2-Ethanediyl)bis[2,5-diethylphospholane] [(S,S)-Et-BPE, 2b] [136779-27-6] C18H36P2 (MW 314.43) InChI = 1S/C18H36P2/c1-5-15-9-10-16(6-2)19(15)13-14-20-17(7-3)11-12-18(20)8-4/h15-18H,5-14H2,1-4H3/t15-,16-,17-,18-/m0/s1 InChIKey = QOLRLVPABLMMKI-XSLAGTTESA-N Physical Data: bp 140–143 °C/0.02 mmHg (distillation through 30 cm Vigreaux column). Solubility: sol in pentane, ether, tetrahydrofuran, toluene, methanol, ethanol. Form supplied in: colorless oil. Purification: obtained from synthesis as a colorless oil, which can be used directly. Analytical samples can be obtained by distillation under high vacuum. Handling, Storage, and Precautions: the ligand should be stored in a tightly sealed container under an inert atmosphere. Prolonged exposure to the atmosphere will cause degradation, as with many other trialkylphosphines. As with other phosphines, these may cause skin and eye irritation, and may be harmful if ingested or inhaled. (2R,2′R,5R,5′R)-1,1′-(1,2-Ethanediyl)bis[2,5-di(2-propyl)phospholane] [(R,R)-i-Pr-BPE, 2c] [528854-34-4] C22H44P2 (MW 370.53) InChI = 1S/C22H44P2/c1-15(2)19-9-10-20(16(3)4)23(19)13-14-24-21(17(5)6)11-12-22(24)18(7)8/h15-22H,9-14H2,1-8H3/t19-,20-,21-,22-/m1/s1 InChIKey = IRVIFEWWPYKALC-GXRSIYKFSA-N Physical Data: mp 68–70 °C. α D 25 − 264 ± 3 ° (c 1, hexane). Solubility: sol in pentane, ether, tetrahydrofuran, toluene, methanol, ethanol. Form supplied in: colorless crystals. Purification: obtained from synthesis as colorless crystals, which can be used directly. Analytical samples can be obtained by recrystallization from ether-methanol at −20 °C. Handling, Storage, and Precautions: the ligand should be stored in a tightly sealed container under an inert atmosphere. Prolonged exposure to the atmosphere should cause degradation, as with many other trialkylphosphine derivatives. As with other phosphines, these may cause skin and eye irritation, and may be harmful if ingested or inhaled. Preparative Methods: preparative methods for the bis(phospholano)ethane (BPE) ligands are dependent upon the availability of chiral 1,4-diols 4, which in some cases can be obtained from baker's yeast reduction of 1,4-diketone 3a, as shown in eq 1 for 2,4-hexanediol.1 Unfortunately, such processes are often limited to single enantiomers of a diol, and to limited alkyl substitution on C1 and C6 of the starting diketone. (1)