Spiro Monophosphite and Monophosphoramidite Ligand Kit

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Spiro Monophosphite and Monophosphoramidite Ligand Kit metals inorganics organometallics catalysts ligands custom synthesis cgm facilities nanomaterials 15-5162 15-5150 15-5156 15-5163 15-5151 15-5157 96-0065 Spiro Monophosphite and Monophosphoramidite Ligand Kit for asymmetric catalytic hydrogenations and other transformations Contains a unit of each of the items listed below. Components available for individual sale. 15-5162 (11a)-()-10,11,12,13-Tetrahydrodiindeno[7,1-de:1,7 -fg][1,3,2]dioxaphosphocin-5-bis[()-1-phenylethyl]amine, min. 98% ()-SIS-E [500997-69-3] 1 kit Technical otes: 1. Chiral ligands for copper-catalyzed asymmetric allylic alkylation with dialkylzincs. 2. Chiral ligands for copper-catalyzed asymmetric conjugate addition of diethylzinc to enones. 3. Chiral ligands for palladium-catalyzed asymmetric hydrosilylation of styrenes 4. Chiral ligands for copper-catalyzed asymmetric ring-opening of oxabicyclic alkenes with Grignard reagents. 5. Chiral ligands for nickel-catalyzed asymmetric hydrovinylation of α-alkyl vinylarenes. 6. Chiral ligands for iridium-catalyzed asymmetric hydrogenation of cyclic enamines. 7. Chiral ligands for iridium-catalyzed asymmetric hydrogenation of cyclic imines. 8. Chiral ligands for gold-catalyzed asymmetric [2 2] cycloaddition reaction. 9. Chiral ligands for rhodium-catalyzed asymmetric hydroacylation of salicylaldehydes to homoallylic sulfides. 10. Chiral ligands for palladium-catalyzed asymmetric carboamination reactions. 0.5 mol% (CuTf) 2.C 6 6 2 mol% SIS-E 2 Zn * diglyme, -30 o C = Cl, Br, I = Et, i r S 2 ' S 2 Tech. ote (1) ef. (1) 11-82% yield of S 2 'S 2 S 2 '/S 2 = 42:58-91:9 47-74% ee for S 2 ' Et 2 Zn 1 mol% Cu(Tf) 2 3 mol% SIS-E toluene, 0 o C 95% yield 97% ee 0.125 mol% [d(p-c 3 5 )Cl] 2 0.5 mol% SIS-E SiCl 3 2 2 SiCl 3 * =, KF/KC 3 Et * 75-99% yield 82-99.1% ee Tech. ote (2) ef. (2) Tech. ote (3) ef. (3) ewburyport, MA 01950-4098 ostfach 1215 Strem Chemicals UK, Ltd. 41 ills oad England CB2 1T

-2-15-5162 (11a)-()-10,11,12,13-Tetrahydrodiindeno[7,1-de:1,7 -fg][1,3,2]dioxaphosphocin-5-bis[()-1-phenylethyl]amine, min. 98% ()-SIS-E [500997-69-3] 2 2 3 3 mol% Cu(Tf) 2 1 6.3 mol% SIS-E toluene, -20 o C 1 MgBr 3 1 =, =, Et, n-bu 2 =,, 3 =, 1 1 2 2 3 3 yield: 54-90% trans/cis: 94:6-99:1 ee: 42-88% Tech. ote (4) ef. (4) 10 mol% [i(allyl)br/sis-e] 10 mol% ab F * C 2 Cl 2, 35 o C (1 atm) 42-96% yield 70-99% ee = Et, n-r, i-r, i-bu, c-c 6 11, C 2 TMS 1 atm 2 [Ir(CD)Cl] 2 /SIS-E TF, 5 mol% I 2, rt (S/C = 100) 1 * 82-97% ee 1 Tech. ote (5) ef. (5,6) Tech. ote (6) ef. (7,8) 2 2 58-98% ee = alkyl 2 (10-50 atm) 0.5 mol% [Ir(CD)Cl] 2 2.2 mol% SIS-E 10 mol% KI, t Bu, rt 16-30 h 88-96% yield 85-99% ee Tech. ote (7) ef. (9). = C 2 or 5 mol% [Au]/SIS-E 5 mol% AgBF 4 C 2 Cl 2, 25 o C 52-87% yield 14-97% ee Tech. ote (8) ef. (10) S S 2.5 mol% [h(cd)cl] 2 5 mol% SIS-E K 3 4, C 2 Cl 2, 30 o C * S S 74-99% yield 36-97% ee Tech. ote (9) ef. (11) Boc 1 2.5 mol% d 2 (dba) 3 7.5 mol% SIS-E a t Bu, toluene, 90 o C Boc 1 61-80% yield 72-94% ee Tech. ote (10) ef. (12,13) eferences: 1. Tetrahedron: Asymmetry 2003, 14, 3867. 8. Adv. Synth. Catal. 2010, 351, 3243. 2. J. rg. Chem. 2003, 68, 1582. 9. ACS Catal. 2012, 2, 561. 3. Tetrahedron: Asymmetry 2004, 15, 2231 10. J. Am. Chem. Soc. 2011, 133, 5500. 4. J. rg. Chem. 2005, 70, 3734. 11. J. Am. Chem. Soc. 2010, 132, 16330. 5. J. Am. Chem. Soc. 2006, 128, 2780. 12. J. Am. Chem. Soc. 2010, 132, 12157. 6. Sci. China Chem. 2010, 53, 1899. 13. rg. Lett. 2011, 13, 2932. 7. J. Am. Chem. Soc. 2009, 131, 1366. ewburyport, MA 01950-4098 ostfach 1215 41 ills oad England CB2 1T

-3-15-5163 (11aS)-(-)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1,7 -fg][1,3,2]dioxaphosphocin-5-bis[()-1-phenylethyl]amine, min. 98% (S)-SIS-E [500997-70-6] Technical ote: 1. See 15-5162. 15-5150 (11a)-()-10,11,12,13-Tetrahydrodiindeno[7,1-de:1,7 -fg][1,3,2]dioxaphosphocin-5-dimethylamine, min. 98% ()-SIS [443965-14-8] Technical otes: 1. Chiral ligands for the rhodium-catalyzed asymmetric hydrogenation of α-dehydroamino esters. 2. Chiral ligands for the rhodium-catalyzed asymmetric hydrogenation of itaconic acid derivatives. 3. Chiral ligands for rhodium-catalyzed asymmetric hydrogenation of β-dehydroaminoesters. 4. Chiral ligands for rhodium-catalyzed asymmetric hydrogenation of enamides. 5. Chiral ligands for rhodium-catalyzed asymmetric auson-khand reaction. 6. Chiral ligands for palladium-catalyzed asymmetric umpolung allylation of aldehydes. C 2 2 (1 atm) 1 mol% [h(cd) 2 ]BF 4 2.1 mol% (S)-SIS C 2 Cl 2, rt C 2 Tech. ote (1) ef. (1) = aryl,, 95.6-99.3% ee C 2 2 C 2 [h(cd) 2 ]BF 4 /(S)-SIS C 2 C 2 Tech. ote (2) ef. (1) =, 94.0% ee =, 94.7% ee 1 C 2 2 2 (100 atm) 2 mol% [h(cd) 2 ]BF 4 4.2 mol% ()-SIS C 2 Cl 2, rt 1 C 2 2 Tech. ote (3) ef. (2) 1 = aryl, 2 =, Et 87-94% ee 2 (50 atm) 1 mol% [h(cd) 2 ]BF 4 2.2 mol% (S)-SIS C 2 Cl 2, 5 o C Tech. ote (4) ef. (3) 91.1-99.7% ee 2 (100 atm) 1 mol% [h(cd) 2 ]BF 4 2.2 mol% (S)-SIS C 2 Cl 2, 0 o C * Tech. ote (4) ef. (2) =, 94% ee = 5-Br, 88% ee = 6-, 95% ee C (1 atm) =, Ts, (Et 2 C) 2 C 3 mol% [h(c) 2 Cl] 2 13.2 mol% ()-SIS AgSbF 6, DCE, 90 o C * 28-73% yield 47-84% ee Tech. ote (5) ef. (4) ewburyport, MA 01950-4098 ostfach 1215 41 ills oad England CB2 1T

-4-15-5150 (11a)-()-10,11,12,13-Tetrahydrodiindeno[7,1-de:1,7 -fg][1,3,2]dioxaphosphocin-5-dimethylamine, min. 98% ()-SIS [443965-14-8] 1 2 3 4 3 eq. Et 3 B 5 mol% d(ac) 2 12 mol% ()-SIS dioxane, 60 o C eferences: 1. Chem. Commun. 2002, 480. 2. J. rg. Chem. 2004, 69, 4648. 3. Angew. Chem., Int. Ed. 2002, 41, 2348. 4. Adv. Synth. Catal. 2005, 347, 759. 5. Tetrahedron: Asymm. 2010, 21, 1216. 2 4 1 3 60-95% yield 46-81% ee Tech. ote (6) ef. (5) 15-5151 (11aS)-(-)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1,7 -fg][1,3,2]dioxaphosphocin-5-dimethylamine, min. 98% (S)-SIS [443965-10-4] Technical ote: 1. See 15-5150. 15-5156 (11a)-()-10,11,12,13-Tetrahydrodiindeno[7,1-de:1,7 -fg][1,3,2]dioxaaphosphocin-5-phenoxy, min. 98% ()-Shi [656233-53-3] Technical otes: 1. Chiral ligands for rhodium-catalyzed arylation of aldehydes with arylboronic acids. 2. Chiral ligands for rhodium-catalyzed arylation of imines with arylboronic acids. 3. Chiral ligands for rhodium-catalyzed arylation of α-ketoesters with arylboronic acids. 4. Chiral ligands for palladium-catalyzed asymmetric umpolung allylation of aldehydes. 5. Chiral ligands for rhodium-catalyzed asymmetric hydrogenation of (Z)-β-arylenamides. 0.5 mol% [hcl(c 2 C 2 ) 2 ] 2 B() 2.1 mol% Shi 2 2 equiv KF = aryl, alkenyl toluene/ 2 (1:1), 0 o C 88-98% yield 62-87% ee 3 mol% h(acac)(c 2 C 2 ) 2 2 1 Ts 2 B() 2 6 mol% Shi 4 equiv KF 1 Ts toluene/ 2 (1:1), 35 o C 56-85% yield 85-96% ee 1 2 B() 2 1 = aryl, alkenyl 2 = Et, i-r, t-bu, h, Bn 1 C 3 mol% [hcl(c 2 C 2 ) 2 ] 2 6 mol% Shi 2 equiv LiF DCE/ 2 (1:4), rt Et 3 B or Et 2 Zn 2 5 mol% [d] 2 10 mol% Shi 1 1 = aryl, alkyl 2 = aryl, methyl =, Ac, h, Cl, Br, ect. 52-97% yield 83-97% ee 2 1 51-96% yield 70-93% ee Tech. ote (1) ef. (1) Tech. ote (2) ef. (2) Tech. ote (3) ef. (3) Tech. ote (4) ef. (4) 2 (50 atm) 1 mol% [h(cd) 2 ]BF 4 2.2 mol% Shi C 2 Cl 2 /toluene, rt, 12 h * 94-96% yield 90-95% ee Tech. ote (5) ef. (5) ewburyport, MA 01950-4098 ostfach 1215 41 ills oad England CB2 1T

-5-15-5156 (11a)-()-10,11,12,13-Tetrahydrodiindeno[7,1-de:1,7 -fg][1,3,2]dioxaaphosphocin-5-phenoxy, min. 98% ()-Shi [656233-53-3] eferences: 1. rg. Lett. 2006, 8, 1479. 2. rg. Lett. 2006, 8, 2567. 3. Angew. Chem. Int. Ed. 2008, 47, 4351. 4. Chem. Sci. 2011, 2, 1135. 5. Tetrahedron 2012, 68, 7685. 15-5157 (11aS)-(-)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1,7 -fg][1,3,2]dioxaphosphocin-5-phenoxy, min. 98% (S)-Shi [885701-71-3] Technical ote: 1. See 15-5156. ewburyport, MA 01950-4098 ostfach 1215 41 ills oad England CB2 1T

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