PhD research with Prof. Lutz H. Gade at the Univ. of Strasbourg. Postdoc in 2003 with Andreas Pfaltz (Basel Switzerland)
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1 idium-catalyzed Asymmetric Isomerization of rimary Allylic Alcohols Mantilli, L., Gerard, D., Torche, S., Besnard, C., Mazet * C. Angew. Chem. Int. Ed., 2009, 48, 1-6 1,n-Glycols as Dialdehyde Equivalents in idium-catalyzed Enantioselective Carbonyl Allylation and Iterative Two- Directional Assembly of 1,3-olyols Lu, Y., Kim, I. S., assan, A., Del Valle, D. J., Krische * M. J. Angew. Chem. Int. Ed., 2009, 48, 1-5
2 Dr. Clément Mazet - University of Geneva D research with rof. Lutz. Gade at the Univ. of Strasbourg ostdoc in 2003 with Andreas faltz (Basel Switzerland) Awarded Marie Curie International utgoing Fellowship in 2006 for work carried out in the Jacobsen Lab.
3 Asymmetric Isomerization BAr F 4 Cy 3 (cod) ( mol%) 1 min 2, TF degassed, 23 o C * TF TF Mazet et al. Tetrahedron Letters 2009, 50, 4141
4 Asymmetric Isomerization [] (5.0 mol%) 1 min 2, TF degassed, 23 o C * (cod) ir BAr F 4 BAr F 4 Cy Cy 2 (cod) BAr F 4 BAr F 4 (cod) a = Cy ; = ir b = tbu ; = ir c = Cy ; = C 2 d = tbu ; = C 2 e = Cy ; = f = tbu ; = g = 1-Ad ; = h = Cy ; = tbu i = tbu ; = tbu j = 1-Ad ; = tbu (cod) (cod)
5 Asymmetric Isomerization (cod) f = tbu ; = g = 1-Ad ; = j = 1-Ad ; = tbu 3 ( mol%) min 2, TF degassed, 23 o C 4 * 3 = ir 4 = 4--C 6 6 g >99% conv 90% ee 3 = tbu 4 = C 6 6 g 80% conv 99% ee 3 = Cy 4 = C 6 6 j 88% conv 98% ee 3 = 4 = C 6 6 f 30% conv 34% ee 3 = C = g 18% conv 25% ee
6 roposed chanism TF TF (Z) (E)! " C=C
7 Conclusion Development of bis-ydride idium Catalyst for Asymmetric lefin Isomerizations Substrate scope very limited, not tolerant to unbranched alkyl substituents roducts generated are equivalent to asymmetric protonation of α,β aldehydes
8 Michael J. Krische B.S. Univ. of California at Berkely Advisor enry apoport Fulbright Fellow, elsinki University 1990.D. Stanford University Advisor Barry Trost I ost-doc., Université Louis asteur - Advisor Jean-Marie Lehn Joined the Faculty at Univ. of Texas at Austin in 2003
9 Enantioselective Carbonyl Allylation ) 2 B C ) 2 2 Brown, J. Am. Chem. Soc. 1983, 2092 i-r 2 C i-r 2 C B n-c Ti(i-r) B 4 (10 mol%) ()-BIL (10% mol%) DCM, -78 o C SnBu 3 offmann, Angew. Chem., Int. Ed. 1978, 768 oush, J. Am. Chem. Soc. 1985, % Yield 86% ee 90% 88% Yield Yield 36% 90% ee ee Umani-onchi J. Am. Chem. Soc. 1993, 7001 Keck J. Am. Chem. Soc. 1993, % Yield 93% ee DCM, -78 o C SiCl 3 Denmark J. Am. Chem. 2001, % Yield 96% ee 85% Yield 87% ee 86% Yield 79 % ee 78% Yield 71% ee
10 idium Catalyzed Transfer ydrogenative Allylation of Allylic Alcohols. Ac [(cod)cl] 2 (2.5 mol% ()-Cl,-BIE (5 mol%) 10 equiv. Cs 2 C 3 (20 mol%) m- 2 Bz (10 mol%) cinnamyl alcohol 72%, 91% ee TF (0.2 M) geraniol 76%, 86% ee 100 o C, 20 hrs nonan-1-ol 72%, 91% ee isobutanol 83%, 94% ee apth apth apth 2 2 X-ray Krische J. Am. Chem. Soc. 2008, 130, 14891
11 Iterative Two-directional Synthesis of 1,3-olyol ot Isolable [{(cod)cl} 2 ] (5 mol%) (S)-Cl,-biphep (10 mol%) Cs 2 C 3 (40 mol%) 4-Cl-3-2 -Bz (20 mol%) dioxane (0.2 M), 90 o C, 3 days Ac (S,S) 70% Yield! 99% ee,! 30:1 d.r. 10 equiv. 51% Yield! 99% ee,! 30:1 d.r. ()-Cl,-biphep (10 mol%) 48% Yield! 99% ee,! 30:1 d.r. 65% Yield! 99% ee, 18:1 d.r. 66% Yield! 99% ee,! 19:1 d.r.
12 Two-Directional Chain Elongation Strategy 1) TS (10 mol%) () 2 C 2 (15 equiv) DCM (0.1 M), 25 o C (S,S) 2) 3, 1:1 DCM/ (0.1 M) -78 o C then ab 4, -78 o C (S,S) (S,S) + [{(cod)cl} 2 ] (5 mol%) ()-Cl,-biphep (10 mol%) Cs 2 C 3 (40 mol%) 4-Cl-3-2 -Bz (20 mol%) TF (0.2 M), 110 o C, 48 hrs As Above () (S) (S) () 75% yield,! 20:1 d.r. 14% mono-allylation Ac (S)-Cl,-biphep (10 mol%) (S) (S) (S) (S) 81% yield,! 20:1 d.r. 12% mono-allylation
13 roposed Catalytic chanism 2 Ac 2 2 I Ac Krische J. Am. Chem. Soc. 2008, 130, 14891
14 roposed Catalytic chanism Ac Ac I 2 2 Ac Ac Ac Krische J. Am. Chem. Soc. 2008, 130, 14891
15 Extension of thodology [{(cod)cl} 2 ] (5 mol%) (S)-Cl,-biphep (10 mol%) Cs 2 C 3 (40 mol%) 4-Cl-3-2 -Bz (20 mol%) dioxane (0.2 M), 90 o C, 3 days 68% Yield! 99% ee,! 30:1 d.r. Ac 10 equiv. As Above 56% Yield! 99% ee,! 30:1 d.r. [{(cod)cl} 2 ] (5 mol%) (S)-Cl,-biphep (10 mol%) MB Bryostatin A ing Ac 72% Yield! 99% ee,! 30:1 d.r. TBS Krische, rg. Lett. ASA
16 Conclusions Two directional assembly of of 1,3-polyols. Although long reaction times, yields and selectivities more than compensate. idium catalyst used for transfer hydrogenative coupling of allyl acetate.
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