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1 Takasago AT (Asymmetric Trasfer ydrogeatio) Catalyst Kit Maufactured uder licese of Takasago patet Takasago AT (Asymmetric Trasfer ydrogeatio) Catalyst Kit Cotais uit of the 12 catalysts listed below. [sde] (p-cymee) [TsDE] (p-cymee) [TsDE] (mesitylee) Ts-DEEB C 3 C 3 C 3 ALL DUCT AVAILABLE ALE U T 1KG Ms-DEEB UCY Ms C 3 C C 3 C(C 3 ) 2 C(C 3 ) C C 3 3 C 3 C C(C 3 ) 2 C(C 3 ) 2 C C(C 3 ) 2 3 C 3 C C 3 3 C 3 C C 3 C 3 Ts Ts 3 C C 3 C C(C 3 ) 2 ALL DUCT AVAILABLE ALE U T 1KG 3 C C 3 Compoets available for idividual sale ewburyport, MA U..A. ax: (978) AT Kit BICEIM race ax: (33) KEL trem Chemicals UK Ltd. trem Chemicals products ewto all, Tow treet ewto, Cambridge CB22 7Ze, UK ax:

2 Chloro{[(1,2)-(-)-2-amio-1,2-dipheylethyl](petafluoropheylsulfoyl)amido}(p-cymee)rutheium(II), mi. 90% [(,)-sdpe](p-cymee) [ ] C ; W: ; orage to brow pwdr. ote: Maufactured uder licese of Takasago patet U B2. Techical ote: 1. ee Chloro{[(1,2)-()-2-amio-1,2-dipheylethyl](petafluoropheylsulfoyl)amido}(p-cymee)rutheium(II), mi. 90% [(,)-sdpe](p-cymee) [ ] C ; W: ; orage to brow pwdr. ote: Maufactured uder licese of Takasago patet U B2. Techical ote: 1. ee Chloro{[(1,2)-(-)-2-amio-1,2-dipheylethyl](4-tolueesulfoyl)amido}(p-cymee)rutheium(II), mi. 95% [(,)-Tsdpe](p-cymee) [ ] C ; W: ; orage to brow pwdr. ote: Maufactured uder licese of Takasago patet U B2. Techical ote: 1. This catalyst has show to effect highly eatioselective hydrogeatio of fuctioalized ketoes where the substituets are dialkylamio, hydoxy, siloxy, carboyl, ester, amide or thioester. C 2 Et Cat. C 2, Et 3 ee up to 99% sy:ati up to >99:1 C 2 Et Tech. ote (1) X Cat. C 2, Et 3 DA/DBU; LiAl 4 or 3 / 2 X 2 Tech. ote (1) ef. (2) = 0,1; = alkyl,, Ac; X = C 2, 2 Cat. C 2, Et 3 EtAc, rt, 7 days 98% ee 2 Tech. ote (1) ef. (3) 0.2 mol% Cat. C 2, DIEA Tech. ote (1) ef. (4-6) 95% ee Cat. C 2, Et 3 Tech. ote (1) ef. (7,8) efereces: 1. Tetrahedro, 2007, 63, Tetrahedro, 2007, 63, Tetrahedro: Asymmetry, 2009, 20, J. rg. Chem., 2009, 74, rg. Lett., 2007, 9, rg. Lett., 2009, 11, Agew. Chem. It. Ed., 2009, 48, Bioorg. d. Chem. Lett., 2008, 18, ewburyport, MA U..A. ax: (978) BICEIM race ax: (33) KEL trem Chemicals UK Ltd. trem Chemicals products ewto all, Tow treet ewto, Cambridge CB22 7Ze, UK ax: AT Kit 0615

3 Chloro{[(1,2)-()-2-amio-1,2-dipheylethyl](4-tolueesulfoyl)amido}(p-cymee)rutheium(II), mi. 90% [(,)-Tsdpe](p-cymee) [ ] C ; W: ; orage to brow pwdr. ote: Maufactured uder licese of Takasago patet U B2. Techical ote: 1. ee Chloro{[(1,2)-(-)-2-amio-1,2-dipheylethyl](4-tolueesulfoyl)amido}(mesitylee)rutheium(II), mi. 90% [(,)-Tsdpe(mesitylee) [ ] C ; W: ; orage pwdr. ote: Maufactured uder licese of Takasago patet U B2. Techical ote: 1. ee Chloro{[(1,2)-()-2-amio-1,2-dipheylethyl](4-tolueesulfoyl)amido}(mesitylee)rutheium(II), mi. 90% [(,)-Tsdpe](mesitylee) [ ] C ; W: ; orage pwdr. ote: Maufactured uder licese of Takasago patet U B Techical ote: 1. Catalyst used i the asymmetric trasfer hydrogeatio of ketoes usig formic acid-triethylamie mixture. * 1 cat C 2 -(C 2 5 ) 3 Tech. ote (1) eferece: 1. J.Am. Chem. oc., 1996, 118, Chloro{()-()-2,2'-bis[di(3,5-yl)phosphio]-1,1'-biaphthyl}[(2)-(-)-1-(4-methoxypheyl)-1 -(4-methoxypheylkC)-3-methyl-1,2-butaediamie]rutheium(II) ()-UCY -XylBIA [ ] C ; W: ; yellow to dark brow/gree solid Maufactured uder licese of Takasago patet applicatio o. J Takasago BIA Diamie Catalyst Kit compoet see (page ). Techical ote: 1. Catalyst used for the rapid, ad highly selective hydrogeatio of ketoes atm, 0.001mol%, 6 mi 2 7 atm, mol%, 15 mi >99% ee "tras- 2 (biap)(daipe) 0.002%, 120 mi" cat. 2, t-buk cat. (0.05mol%) 2 (10 atm), DBU Tech ote (1) Tech. ote (1) >95% ee cat. (0.05mol%) 2 (10 atm), t-buk * Tech. ote (1) "tras- 2 (biap)(daipe) 0.1mole%, 42% yield, 90% ee" 97% ee ewburyport, MA U..A. ax: (978) AT Kit BICEIM race ax: (33) KEL trem Chemicals UK Ltd. trem Chemicals products ewto all, Tow treet ewto, Cambridge CB22 7Ze, UK ax:

4 (cot.) Chloro{()-()-2,2'-bis[di(3,5-yl)phosphio]-1,1'-biaphthyl}[(2)-(-)-1-(4-methoxypheyl)-1 -(4-methoxypheyl-kC)-3-methyl- 1,2-butaediamie]rutheium(II) ()-UCY -XylBIA [ cat. (0.002mol%) 2 (10 atm), t-buk * Tech. ote (1) "tras- 2 (biap)(daipe) 0.005mole%, 50% yield, 86% ee" eferece: 1. atet Applicatio o. J % ee Chloro{()-(-)-2,2'-bis[di(3,5-yl)phosphio]-1,1'-biaphthyl}[(2)-()-1-(4-methoxypheyl)-1 - (4-methoxypheyl-kC)-3-methyl-1,2-butaediamie]rutheium(II) ()-UCY -XylBIA [ ] C ; W: ; yellow to dark brow/gree solid ote: Maufactured uder licese of Takasago patet applicatio o. J Takasago BIA Diamie Catalyst Kit compoet see (page ). Techical ote: 1. ee Chloro{-[(1,2)-1,2-dipheyl-2-(2-(4-methylbezyloxy)ethylamio)-ethyl]-4-methylbezee sulfoamide(chloro)rutheium(ii) (,)-Ts-DEEB [ ] C ; W: ; gray to brow pwdr. ote: Maufactured uder licese of Takasago patet applicatio CT/J2011/ Techical otes: 1. Catalyst used for asymmetric -trasfer hydrogeatio. C 2 /Et 3 = 5/2 (2M) (,)--cat 60 C (/C=30,000, 96h) 95% cov. 97% ee (/C=1,000, 5h) >99% cov. 97% ee (>95% select.) (/C=500, 24h) >99% cov. 95% ee Tech. ote (1) C (/C=1,000, 5h) >99% cov. 95% ee (/C=1,000, 24h) >99% cov. 93% ee (/C=1,000, 5h) 98% cov. 96% ee 2. Catalyst used for asymmetric 2 hydrogeatio. 2 (3 Ma) (,)--cat, 60 C Tech. ote (2) (/C=1,000, 20h) >99% cov. 99% ee (/C=5,000, 18h) >99% cov. 93% ee ewburyport, MA U..A. ax: (978) AT Kit BICEIM race ax: (33) KEL trem Chemicals UK Ltd. trem Chemicals products ewto all, Tow treet ewto, Cambridge CB22 7Ze, UK ax:

5 (cot.) 3. Catalyst used for dyamic kietic resolutio Chloro{-[(1,2)-1,2-dipheyl-2-(2-(4-methylbezyloxy)ethylamio)-ethyl]-4-methylbezee sulfoamide(chloro)rutheium(ii) (,)-Ts-DEEB [ ] C 2 /Et 3 = 5/2 (2M) (,)--cat DM, 60 C (/C=10,000, 32h) >99% cov. (dl:meso = 97.2:2.8 >99% ee (dl) eferece: 1. J. Am. Chem.oc., 2011, 133, Tech. ote (3) [(1,2)-1,2-Dipheyl-2-(2-(4-methylbezyloxy)ethylamio)-ethyl]-4-methylbezee sulfoamide(chloro)rutheium(ii) (,)-Ts-DEEB [ ] C ; W: ; gray to brow pwdr. ote: Maufactured uder licese of Takasago patet applicatio CT/J2011/ Techical ote: 1. ee Chloro{-[(1,2)-2-[()-[2-[[1,2,3,4,5,6-η)-4-methylpheyl]methoxy]ethyl]amio]-1,2- dipheylethylmethaesulfoamidato}rutheium(ii) -(,)-Ms-DEEB [ ] C ; W: ; light to dark brow pwdr. ote: Maufactured uder licese of Takasago patet applicatio CT/J2011/ Chloro{-[(1,2)-2-[()-[2-[[1,2,3,4,5,6-η)-4-methylpheyl]methoxy]ethyl]amio]-1,2- dipheylethylmethaesulfoamidato}rutheium(ii) -(,)-Ms-DEEB [ ] C ; W: ; light to dark brow pwdr. ote: Maufactured uder licese of Takasago patet applicatio CT/J2011/ ewburyport, MA U..A. ax: (978) AT Kit BICEIM race ax: (33) KEL trem Chemicals UK Ltd. trem Chemicals products ewto all, Tow treet ewto, Cambridge CB22 7Ze, UK ax:

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