When something goes wrong. Goya: Mother showing her derformed child to two women Louvre, Paris
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1 1 ew Catalytic Asymmestric eactions Karl Anker Jørgensen Danish ational eserach Foundation: Center for Catalysis Department of Chemistry, Aarhus University Denmark When something goes wrong 2 Goya: Mother showing her derformed child to two women Louvre, Paris
2 3 A failed reaction Et (II) Et SnCl 4 Toluene Et ot formed Et >90% yield Chem. Commun. 1999, 1869 Catalytic asymmetric aza-friedel-crafts reactions 4 Ar 1 2 Chiral Catalyst C2 1 Ar C 2 2 Cl Cl 2C X 2 S C 2 Ac Vancomycins Cephaloglycin 2C 2 C 2 2 C 3 M e ocardicin A Aspartame analogue
3 ptically active aromatic a-amino acids 5 1 Ar Bn P P Bn Chiral Catalyst 1 2 C 2 1 Ar C C 2 2 C 2 2 = M e: TMSI, 90% yield = E t : TMSI, 83% yield = Bn: 2, P d(ac) 2, 98% yield = t Bu: TFA, Quantitative yield C C C C C2 2 I then TMS3 92% yield BF 4 then 3 P 2, 2 83% yield Angew. Chem. Int. Ed. 2000, 39, 4114 J. rg. Chem. 2002, 67, 4352 Scope and potential 6 Ar Pg CEt ()-Tol-BIAP-PF6 Ar Pg C2Et Ar Ar P (I) P Ar Ar C2 C2 C2 C 2 C2 C 2 Et C2 C % yield 98% ee 81% yield 96% ee 88% yield 86% ee 79% yield 98% ee C 2 C2 2 C 2 C 2 C2 C2 C2 S C 2 Bn C2M e C 2 86% yield 92% ee 75% yield 92% ee 63% yield 96% ee 40% yield 95% ee 75% yield 94% ee
4 chanistic Considerations 7 2 C C 2 Catalyst 2 C C 2 Et igh Discr imination eactive e-face tbu Et Low discrimination Catalytic asymmetric Friedel-Crafts alkylation reactions 8 Cat. 10 mol% C M X X M = (II), X = Tf (C2Cl2): 100% conversion, 88% ee M = (II), X = Tf (Et2): 100% conversion, 97% ee M = Zn(II), X = Tf (C 2 Cl 2 ): 100% conversion, 87% ee Tf Tf 100% conversion, 42% ee Angew. Chem. Int. Ed. 2001, 41, 160
5 Cat mol% =, alkyl 2 =, Cl, C 3 =, 4 = Ar, alkyl, C2Bn C 70-96% yield 80->99.5% ee 1 4 Cat mol% 4 1 C >90% yield >79% ee 4 = Ar, alkyl, C 2 Bn M e M e 4 Cat mol% 4 4 = Ar, alkyl C 65-68% yield 60-89% ee Catalytic enantioselective Friedel-Crafts reactions a simple approach to optically active α-aromatic α-hydroxy carboxylic acids 10 CEt 2 Cat 10 mol% 2 Et C 2 Cl 2 : 85% yield, 70% ee TF: 82% yield, 94% ee Et2: 92% yield, 90% ee (II) t- Bu TBS Et Et a, b, c = : 92% yield = : 95% yield 2 a) PI, TMS3 b) sat. ac3 (aq) c) 10% Cl/Et J. Am. Chem. Soc. 2000, 122, J. rg. Chem. 2001, 66, 1009
6 Scope and potential 11 CEt 2 X Cat 10 mol% Et X 2 >80 yield, >85% ee Et CEt ( C2)n Cat 10 mol% ( C 2 ) n n = 1: 54% yield, 85% ee n = 2: 56% yield, 93% ee Pg Et xidation Pg Et Catalytic asymmetric tandem reactions formation of optically active dihydro-benzopyrans 12 2 X 1 C X C 2 C X 1 C 2 X 1 X C2 X =, Ar C 2 M gx2-bx X Ar high yield, one diastereomer ee up to 85% ()-4a: = (S)-4b: = (S)-4c: = 1-p Submitted 2002
7 Discovery of a direct aldol reaction 13 2 Et 5 eqv. Chiral LA Chiral LA Et 2 ot formed Et 2 C C 2 Et (Tf) t -Bu 2 14 A catalytic asymmetric homo-aldol reaction Et Chiral LA Et 2 C C 2 Et Et 3/TBSCl C 2 Et TBS 49% yield from EPV (Tf) 2 (SbF 6 ) 2 Amine [mol%] Ee [%] Amine [mol%] Solvent Ee [%] - ( )-65 - Et 2 ( )-50 2 /10 ( )-79 2 /10 C 2 Cl 2 ()-63 2 /5 ( )-96 Bn 2 /10 C 2 Cl 2 ()-75 Bn 2 /10 ( )-93 Cy 2 /10 C 2 Cl 2 ()-77 Et( i Pr) 2 /10 ( )-67 Chem. Commun. 2000, 2211
8 The concept 15 Et 2 Et 2 Et 2 Electrophilic carbon ucleophilic carbon 16 Catalytic asymmetric direct Mannich reactions Et 2 C Pg C 2Et Chiral LA Pg Et 2 C C 2 Et Imine candidates C 2 Et S C 2 Et C 2Et Angew. Chem. Int. Ed. 2001, 40, 2995
9 17 ptimisation of the direct Mannich reaction Et 2 C C 2 Et Catalyst Et 2 C C 2 Et (Tf) 2 C 2 Cl 2 76% yield -33% ee (Tf) 2 C 2 Cl 2 TF 44% yield 16% yield 12% ee 33% ee C 2 Cl 2 70% yield 89% ee (Tf) 2 TF 45% yield 76% ee 18 Scope of the direct Mannich reaction Et 2 C C 2 Et (Tf) 2 C 2 Cl 2 Et 2C C 2Et Et 2C C 2Et Et 2C C 2Et Et 2C Bn C 2Et Et 2C Br C 2Et 70% yield 89% ee 89% yield >10:1 dr >98% ee 94% yield >10:1 dr 97% ee 79% yield 3:1 dr 78% ee
10 eduction of the Mannich product 19 L-Selectride Et 2 C C 2 Et TF -78 C, 90min Et 2 C C 2 Et PTSA 70 C 4h C 2 Et = : 92% yield one diastereomer = Bn 70% yield one diastereomer 20 Detosylation C 2 Et Boc 2 / DMAP C, r.t. 98% Boc C 2 Et Boc C 2 Et Mg/ /TF=3:1 Sonication 60 min 71% Boc C 2
11 21 Proposed chanism Et Et Et Et Malonic esters and b-keto esters as nucleophiles in direct Mannich reactions 22 Et Et C 2 Et (Tf) 2 (10 mol%) C 2 Cl 2 Et 2 C C 2 Et C 2Et =, n-bu, i-bu, Bn Yields: >80%; >85% ee 1 2 C 2Et (Tf) 2 C 2 Cl C C 2 Et 2 1 = 2 = : 87%, 93:7 dr, 88% ee 1 = Et, 2 = : 80%, 98:2 dr, 92% ee 1 = i-pr, 2 = : 55%, 84:16 dr, 91% ee 1 = Bn, 2 = : 83%, 96:4 dr, 93% ee 1 =, 2 = allyl: 69%, 92:8 dr, 87% ee 1 = 2 = (C 2 ) 4 : 89%, 99:1 dr, 86% ee Submitted for publication
12 Catalytic asymmetric direct a-amination 23 Et 2 C (Tf) 2 C 2 Cl 2 Et 2 C C 2 2 C C 2Et 2 2 C C 2 2 Catalyst 1 C 2Et 2 2 C C 2 2 L-Selectride -78 C 2 2C 1 C 2 1) 0.5 a 2) TMSC 2 1 C 2Et 2 2 C C 2 2 J. Am. Chem. Soc. 2002, 124, ptimisation of the direct a- amination reaction C 2Et Bn 2C C 2Bn Catalyst Bn 2 C C 2 (Tf) 2 C 2 Cl 2 TF 39% yield 60% yield 90% ee 82% ee (Tf) 2 C 2 Cl 2 55% yield 77% ee TF 57% yield 89% ee (Tf) 2 C 2 Cl 2 TF 50% yield 58% yield 70% ee 88% ee
13 Scope of the direct a-amination reaction 25 (Tf) 2 (Tf)2 C 2 C 2 Cl 2 TF 39% yield 57% yield 90%ee 89%ee C 2 Cl 2 45% yield 90%ee C 2 C511 C 2 Cl 2 78% yield 92%ee C 2 C 2 Cl 2 48% yield 97%ee C 2 Cl 2 62% yield 93%ee C 2 C2 C2 C2 C2 C 2 Cl 2 52% yield 92%ee C 2 Cl 2 53% yield 96%ee C 2 Cl 2 78% yield 95%ee TF 72% yield 96%ee 26 Synthesis of oxazolidinones Bn 2C C 2 1) Pd/C 2 2) Zn acetone Ac C 2 88% yield Bn 2C C 2 1) Pd/C 2 2) Zn acetone Ac C 2 89% yield
14 27 Synthesis of syn-a-hydroxy-b-amino acids C 2Et Catalyst C 2Et L-Selectride -78 C C 2 Boc 33% yield 1) a-i 2 2) Boc 2 DMAP 3) a C 2 Et 28 = i-pr; KI-1230 = c-hexyl; KI Microginin C 2 i-pr 2 C 2 Amastatin Va l-val-asp- 2 C Boc 2 C 2 Valinoctin A ABT-271 Bestatin 2 Bz Ac
15 29 Proposed mechanism Et Et Bn Et Catalytic asymmetric direct a-amination of b-keto esters optically active b-ketoand b-hydroxy-a-amino acids 30 Et 1 2 (Tf) 2 C 2 Cl 2 Et 2 1 Et 1 2 Et 2 Et Submitted for publication
16 Scope 31 Et CBz 81% yield, 98% ee Et Et CBz 94% yield, 98% ee Et CBz 88% yield, 98% ee n ( 2 C) Et CBz n = 1: 99% yield, 99% ee n = 2: 94% yield, 98.5% ee n = 2: 92% yield, 98% ee 32 rgano Catalytic Aldol eaction: Type I Aldolase tal Catalysed Aldol eaction: Type II Aldolase
17 L-Proline catalysed asymmetric a-amination of aldehydes 33 Et 2 C C 2 Et C 2 C 2 Et C 2 Et Et Et Solvent L-Proline (mol%) eaction time [min] Yield [%] ee [%] C2Cl C2Cl C2Cl C EtAc Angew. Chem. Int. Ed. 2002, 41, 1790 (rec ) List, J. Am. Chem. Soc. 2002, 124, 5656 (rec ) Scope of the L-proline catalysed asymmetric a-amination of aldehydes C L-Proline C 2 2 C 2 2 C ab 4 C 2 2 a C 2 2 C C2 Et Yield 67% ee 93% Et C2 Et Yield 77% ee 95% C2 Et i-pr Yield 83% ee 93% C 2 Et C 2 Et C 2 Et C 2 Bn Bn i-pr Yield 57% ee 91% Yield 92% ee 93% Yield 68% ee 89% Yield 70% ee 91%
18 35 Product modification / Determination of absolute configuration ipr 1) 2 /Pd-C 2) Zn/acetone-Ac ipr ipr Boc Boc 1) KMn 4 oxidation 2) TMSC 2 3) TFA 4) 2 /a-i 5) (Boc) 2/DMAP ipr Boc L-proline catalysed asymmetric a- amination of ketones 36 C 2 Et 2 C 1 (10 mol%) 2 C 2 Et 1 C C 2 Et C 2 Et 2 C 2Et C2 Et 2 for 1 = C 2 Et C 2 Et egioselectivity: 91:9 Yield: 80% ee: 95% C 2 Et C 2 Et i-pr egioselectivity: 76:24 Yield: 69% ee: 99% C 2 Et C 2 Et Et egioselectivity: 81:19 Yield: 77% ee: 98% Et C 2 Et C 2 Et Yield: 79% ee: 94% C 2 Et C 2 Et Bn egioselectivity: 82:18 Yield: 92% ee: 95% C 2 Et C 2 Et Yield: 67% ee: 84% J. Am. Chem. Soc. 2002, 124, 6254
19 37 Stereoselective formation of optically active oxazolidinones 1) ab 4 2) 0.5 a C 2Et C2 Et Bn 1) TiCl 4/Et 3Si 2) 0.5 a 1) TMSI C 2 Et 2) Acetone 3) Zn/Ac Bn C 2 Et Bn Bn The first organo-catalytic inverse-electron demand hetero-diels-alder reaction direct evidence for enamine intermediate 38 Enamine intermediate ' Electron-rich alkene ucleophile 2 EWG 2 EWG EWG 2 Submitted for publication
20 39 Further into the mechanism 2 EWG 2 EWG Silica 2 EW G 2 EWG 2 EW G EWG 2 40 Screening of catalysts i-pr P h C2 Cat. 10 mol% S ilica i-pr C2 P CC 2 EWG C 2 C 2 low yield low yield low yield 5% yield 64% ee C 2 15% yield 47% ee C 2 C2 C2 i-pr Bn 9% yield 20% ee 9% yield 22% ee C % yield 8% ee 69% yield 51% ee 54% yield 56% ee 28% yield 75% ee low yield 46% yield 88% ee 69% yield 92% ee
21 41 Potential of the reaction 1 C mol% Silica 1 2 C 2 3 ne diastereomer Yield [%] ee [%] Et i-pr Bn Et 4-Cl i-pr 4-Cl i-pr Et Catalytic asymmetric enry reactions a simple approach to optically active β-nitro and β-amino α-hydroxy carboxylic acids Et Chiral LA 2 Et 2 C C 2 Et ot formed 2 Et igh yield and enantioselectivity
22 Catalytic Enantioselective enry eaction of 2-Keto Esters 43 Et C 2 2Et (Tf) 2 2 Et 3 C 2Et 2 Yield: 95% ee: 92% Et C 2Et 2 Yield: 73% ee: 87% C 2Et 2 Yield: 47% ee: 77% C 2Et C Yield: 91% ee: 93% C 2 Et 2 Yield: 97% ee: 94% C 2 Et 2 Yield: 92% ee: 94% C 2 Et 2 Yield: 90% ee: 94% i-bu C 2 Et 2 Yield: 99% ee: 92% C 2 Et 2 Yield: 81% ee: 86% C 2 Et C 2 Et 2 Cl 2 Yield: 91% 2 Yield: 99% ee: 88% ee: 93% C 2 Et 2 Yield: 68% ee: 57% Chem. Commun. 2001, 2222 J. rg. Chem. 2002, 67, eduction of nitro functionality Cl C2Et 2 C 2Et 2 a-i / 2 (atm) a-i / 2 (atm) Cl C2Et 2 C 2 Et 2 Boc2, cat. DMAP CCl2 C 2Et Boc Et 2C Cl
23 45 Proposed mechanism t-b u C u Tf Tf C 2Et M e -2 Tf Et 3 C u Et Et Et 3 Tf Et3 C 2 Et 2 C 2Et C u Et The catalytic enantioselective aza-enry reaction a simple approach to optically active β-nitro and β-amino α-amino carboxylic acids 46 C2Et TMS P h (Tf) mol%/- 100 C PMP C2Et PMP PMP P MP PMP 2 Et C2E t 2 C 2 E t 2 C 5 11 C 2 Et 2 Bn C 2 Et 94% yield 25:1 dr 95% ee 67% yield 5:1 dr >98% ee 87% yield 39:1 dr 83% ee 93% yield 32: 1 dr 88% ee 2 Et PMP C 2 E t 2/a-i PM P 2 C 2 Et E t J. Am. Chem. Soc. 2001, 123, 5843
24 The catalytic asymmetric nitro-mannich reaction 47 P g Et 2 P h M e Pg M e Tf Tf M e Et - 2 Tf P g Pg Et Et C 2 2 Et C 2 Pg P h PMP C 2 Et 2 2 Et 3 (20%) room t emp ambient conditions P MP Cat. C2Et = : 38% yield, 97% ee = : 61% yield, 7: 3 dr, 99% ee = Et: 81% yield, 95: 5 dr, 97% ee = Pentyl: 52% yield, 93:7 dr, 97% ee = Bn: 80% yield, 95:5 dr, 95% ee = : 59% yield, 55:45 dr, 74% ee E t 3 Angew. Chem. Int. Ed. 2001, 40, 2992 Acknowledgements 48 Sorin Aburel Pay Bayon Anders Bøgevig Christina Christensen Xiangming Fang icholas Gathergood Kurt V. Gothelf ita G. azell Anne K. Jensen Kim B. Jensen Karsten Juhl Kristian. Knudsen agaswamy Kumaragurubaran ester V. Lingen Mauro Marigo agatoshi ishiwaki Tine isgaard Mark oberson Steen Saaby Wei Zheng Danish ational esearch Foundation
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