Rhodium-Catalyzed Enantioselective
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1 Rhodium-Catalyzed Enantioselective Isomerization of Oxabicycles Reporter: Jie Wang Checker: Shubo Hu Date: Yen, A.; Choo, K.-L.; Yazdi, S. K.; Franke, P. T.; Webster, R.; Franzoni, I.; Loh, C. C. J. Poblador-Bahamonde, A. I.; Lautens, M. Angew. Chem. Int. Ed. 2017, 56, 6307.
2 Contents 1 Introduction 2 Intramolecular ARO via Cycloisomerization 3 Enantioselective Isomerization of Oxabicycles 4 Summary 2
3 CV of Mark Lautens Education: BS B.S.,., University of Guelph (1981) Ph.D., University of Wisconsin-Madison with Trost, B. M. ( ) 1985) Postdoctoral Fellow., Harvard University with Evans, D. A. ( ) 1987) Mark Lautens University of Toronto ( ) Research: Asymmetric catalysis with focus on rhodium, nickel Reactions of organosilicon and organotin compounds Fragmentation reactions 3
4 Introduction Intermolecular asymmetric ring opening (ARO) reactions: Lautens, M. et al. Acc. Chem. Res. 2003, 36, 48. 4
5 Introduction Lautens, M. et al. Acc. Chem. Res. 2003, 36, 48. 5
6 Intramolecular ARO Lautens, M. et al. Angew. Chem. Int. Ed. 2016, 55,
7 Evaluation Conditions entry [Rh]/L (x/y) solvent T( o C) yield (%) ee (%) 1 [Rh(cod)Cl] 2 /L (4/8) THF ND 2 [Rh(cod)OH] 2/L (4/8) THF 80 5 ND 3 Rh(cod) 2 OTf/L (5/6) THF 80 > [Rh(cod)Cl] 2 /L (4/8) AgOTf, TBAI THF ND 5 Rh(cod) 2 OTf/L (5/6) DCE Rh(cod) 2 OTf/L (5/6) Dioxane 80 > Rh(cod) 2 OTf/L (5/6) Toluene 80 > Rh(cod) 2 OTf/L (5/6) MeCN 80 - Decomp. 9 Rh(cod) 2 OTf/L (5/6) THF 50 >99 >99 7
8 Substrate Scope 8
9 Mechanistic Basis of the PKR 9
10 Substrate Scope of PKR 10
11 Control Experiments 11
12 Perturbation Experiments with ROH entry ROH (equiv.) a yield (ee) b yield (ee) c yield (ee) 1 NO ROH 97 (>99) MeOH (5) 45 (>99) 40 (>99) Traces 3 MeOH (20) 29 (>99) 54 (>99) 14 (97) 4 MeOH (50) 15 (>99) 59 (>99) 24 (99) 5 MeOH (100) 9 (>99) 54 (>99) 33 (97) 6 MeOH (neat) - 39 (>99) 50 (97) 7 t BuOH 80 (>99) 19 (>99) - 12
13 Diastereoselective Hydrogenation OH OH H O OH H 2,Pd/C(10mol%) EtOAc, salt ice Bath H O OH >99% ee 92% yield, 98% ee 13
14 Isomerization of Oxabicycles OR O OR [Rh(cod) 2 ]OTf (5 mol%) (R,S)-PPF-P t Bu 2 (6 mol%) RO 1,4-dioxane, 50 o C or 80 o C O RO up to 99% yield up to 99% ee Lautens, M. et al. Angew. Chem. Int. Ed. 2017, 56,
15 Evaluation of the Catalysts entry [Rh]/L (x/y) yield (%) ee (%) 1 Rh(cod) 2 OTf/L (5/6) [Rh(cod)Cl] 2 /L (2.5/6) NR ND 3 [Rh(cod)OH] 2 /L (2.5/6) NR ND 4 Rh(cod) 2 OTf/L (2/3) <1 ND 5 Rh(cod) 2 OTf/L (3/4) 43 ND 15
16 Evaluation of the Solvents entry solvent yield (%) ee (%) 1 THF ,4-dioxane MeCN NR ND 4 DCE PhMe NR ND 6 DCM DMAc <1 ND 16
17 Substrate Scope entry R yield (%) ee (%) 1 CH 3CO t BuOCO C 6 H 5 CO MeOC 6 H 4 CO 92 > BrC 6 H 4 CO 56 > MeSC 6 H 4 CO ThienylCO C 6 H 5 NHCO
18 Substrate Scope entry R yield (%) ee (%) 1 C 6 H 5 CH BrC 6 H 4 CH CF 3 C 6 H 4 CH (MeCOO)C 6 H 4 CH MeSC 6H 4CH MeOC 6 H 4 CH
19 Gram-Scale Synthesis 19
20 Enantioselective Methanolysis 20
21 Epoxides in ARO 21
22 Participation of the Rhodium Catalyst entry [Rh] PPF-P t Bu 2 solvent result 1 Yes (R,S) MeOH 63% 2 No No MeOH NR 3 Yes No MeOH decomposition 4 Yes (S,R) 1,4-dioxane (50 eq. MeOH) NR 5 Yes (S,R) MeOH 26% recovery 6 Yes (R,S) 14-dioxane 1,4 80% recovery 22
23 Proposed Mechanism 23
24 Summary Lautens, M. et al. Angew. Chem. Int. Ed. 2016,, 55,, Lautens, M. et al. Angew. Chem. Int. Ed. 2017, 56,
25 The first paragraph The rhodium-catalyzed asymmetric ring-opening (ARO) reaction of oxabicyclic alkenes offers a facile entry into chiral hydronaphthalene hth frameworks thatt are ubiquitous it motifs found in a wide variety of biologically active natural products. For this reason, the development of the ARO reaction represents an area of increasing interest by various research groups, with many new methodologies emerging over the past two decades since we first disclosed this transformation. 25
26 The last paragraph In summary, we have demonstrated t d the first rhodium catalyzed enantioselective isomerization of meso-oxabenzonorbornadienes to 1,2-naphthalene oxides. This methodology delivers potentially useful building blocks in moderate to excellent yields with consistently impressive enantioselectivities. Efforts to access enantioenriched products from the stereospecific ring-opening reactions of this class of compounds are underway in our laboratories. 26
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