Asymmetric Allylic Alkylation of Ketone Enolates: An Asymmetric Claisen Surrogate.
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1 Asymmetric Allylic Alkylation of Ketone Enolates: An Asymmetric Claisen Surrogate. Erin C. Burger and Jon A. Tunge* Department of Chemistry, University of Kansas, Lawrence, KS 0 Supporting Information Experimental Materials. Benzene was dried over sodium metal. All other materials were used as received. β-ketoesters a-h were prepared by the addition of diketene to the corresponding allylic alcohols. β-ketoester f was prepared by the DMAP catalyzed condensation of β-ketoethylester and allylic alcohol. β-ketoesters i-l were prepared by the condensation of the corresponding acid chloride with Meldrum s acid followed by addition of the appropriate allylic alcohol. H NMR spectra were obtained on a Bruker Avance 00 or a Bruker Avance 00 DRX spectrometer and referenced to residual protio solvent signals. Structural assignments are based on H, C, DEPT-, COSY, and HMQC spectroscopies. General procedure for catalytic rearrangements: In a Schlenk tube under Ar, allylβ-ketoester (. mmol) and either Pd(PPh ) (0 mol %) or the combination of Pd (dba) ( mol %) and Trost ligand (0 mol %) were dissolved in ml of benzene. The reaction was allowed to stir under Ar for the reported time. Following solvent evaporation the crude product was purified via flash chromatography (SiO, 0% Et O: Hex). Collado, I.; Pedregal, C.; Mazon, A.; Espinosa, J. F.; Blanco-Urgoiti, J.; Schoepp, D. D.; Wright, R. A.; Johnson, B. G.; Kingston, A. E. J. Med.Chem. 00,, -. Gilbert, J. C.; Kelly, T. A. J. Org. Chem.,, -0. Svenstrup, N.; Simonsen, K.; Thorup, N.; Brodersen, J.; Dehaen, W.; Becher, J. J. Org. Chem.,, -0. Yuste, F.; Brena, F.; Barrios, H.; Sanchez-Obregon, R.; Ortiz, B.; Walls, F. Synth. Commun.,, -. S-
2 O a 0 S-
3 a yellow oil: H NMR (00 MHz, CDCl ) δ.0 (m, 0H: arom H),. (m, H: ambiguous CH=),. (app. q, J = Hz, H: CH),.0 (dd, J = Hz, Hz, H: diastereotopic CH ). (dd, J = Hz, Hz, H: diastereotopic CH ),. (s, H: CH ). C NMR ( MHz, CDCl ) δ 0. (C=O),. (arom. C),. (arom. C),. (CH=), 0. (CH=),. (arom. CH),. (arom. CH),.0 (arom. CH),. (arom. CH),. (arom. CH),. (arom. CH),. (CH ),. (CH),.0 (CH ). IR (CH Cl ): ν max 0, 0,. HRMS calcd for C H O [M+] 0., found 0.. O b Oi, S.; Honma, Y.; Inoue, Y. Org. Lett. 00,,. S-
4 b clear oil: H NMR (00 MHz, CDCl ) δ. (m, H: =CH-CH ),. (dd, J = Hz, Hz, H: =CH-CH),. (app. sep, J = Hz, H: =CH-CH ),. (dd, J = Hz,. Hz, H: diastereotopic CH ),. (dd, J = Hz,. Hz, H: diastereotopic CH ),. (s, H: (C=O)CH ),. (d, J = Hz, H: =CH-CH ),.00 (d, J = Hz, H: CH-CH ). Tsuji, J.; Yamada, T.; Minami, I.; Yuhara, M.; Nisar, M.; Shimizu, I. J. Org. Chem.,, -. S-
5 C NMR ( MHz, CDCl ) δ 0. (C=O),.0 (=CH-CH),. (=CH-CH ),.0 (CH ),. (=CH-CH), 0.0 ((C=O)CH ), 0. (CH-CH ),. (=CH-CH ). IR (CDCl ): ν max 0,,. HRMS calcd for C H O [M+H]., found.0. GC (Chiraldex B-TA : Hold 0 o C for min., ramp o C /min to o C) t r =.,. min. c O c clear oil: H NMR (00 MHz, CDCl ) δ. (m, H: =CH),. (m, H: =CH),. (m, H: CH),. (dd, J = Hz,. Hz, H: diastereotopic (C=O)CH ),. (dd, J = Hassner, A. Naumann, F. Chem. Ber.,, -. S-
6 Hz,. Hz, H: diastereotopic (C=O)CH ),. (m, H: ambiguous CH ),. (s, H: CH ),. (m, H: ambiguous diastereotopic CH ),. (m, H: ambiguous diastereotopic CH ). C NMR ( MHz, CDCl ) δ 0.0 (C=O),.0 (.) (=CH),. (.) (=CH), 0. ((C=O)CH ),. (CH),. (ambiguous CH ), 0.0 (CH ), 0.0 (ambiguous CH ). IR (CDCl ): ν max 00, 0,. HRMS calcd for C H O [M+H].0, found.00. GC (Chiraldex B-TA : Hold 0 o C for min., ramp 0. o C/min to o C) t r =.,. min. d O 0 S-
7 d clear oil: H NMR (00 MHz, CDCl ) δ. (m, H: =CH),. (m, H: =CH),. (m, H: =CH-CH),. (dd, J = Hz,. Hz, H: diastereotopic (C=O)CH ),.0 (dd, J = Hz,. Hz, H: diastereotopic (C=O)CH ),. (s, H: CH ),. (m, H: ambiguous CH ),. (m, H: ambiguous diastereotopic CH ),. (m, H: ambiguous diastereotopic CH ),. (m, H: ambiguous diastereotopic CH ),. (m, H: ambiguous diastereotopic CH ). C NMR ( MHz, CDCl ) δ 0. (C=O), 0. (.) (=CH),. (.) (=CH), 0. ((C=O)CH ),. (CH), 0. (CH ),. (.,.) (ambiguous CH ),. (.) (ambiguous CH ),. (.,.) (ambiguous CH ). IR (CDCl ): ν max 00, 0,. HRMS calcd for C H O [M+H]., found.. GC (Chiraldex B-TA : Hold 0 o C for min., ramp 0. o C/min to o C) t r =.,. min. e O Monti, S.; Cowherd, F. G.; McAninch, T. W. J. Org. Chem., 0, -. S-
8 e clear oil: H NMR (00 MHz, CDCl ) δ. (m, H: =CH-CH ),. (dd, J = Hz, Hz, H: =CH-CH),. (m, H: CH),. (dd, J = Hz,. Hz, H: diastereotopic (C=O)CH ),. (dd, J = Hz,. Hz, H: diastereotopic (C=O)CH ),. (s, H: CH ),. (m, H: ambiguous CH ),. (m, H: ambiguous diastereotopic CH ),. (broad m, H),. (m, H: ambiguous CH ). C NMR ( MHz, CDCl ) δ 0. (C=O),.0 (=CH-CH),. (=CH-CH ),.0 ((C=O)CH ),. (CH),. (.,.) (ambiguous CH ), 0. (CH ), 0. (ambiguous CH ),.0 (ambiguous CH ),.0 (ambiguous CH ). IR (CDCl ): ν max 0, 0,. HRMS calcd for C 0 H O [M+H]., found.. GC (Chiraldex B-TA : Hold 0 o C) t r =.,. min. S-
9 O f 0 S-
10 f clear oil: H NMR (00 MHz, CDCl ) Major Diastereomer: δ. (overlapping multiplet, H: =CH-CH ),. (ddd, J = Hz, Hz, Hz, H: =CH-CH),. (app. hex, J = Hz, H: CH-CH ),. (overlapping multiplet, cyclohexyl CH ),. (m, H: (C=O)CH),. (overlapping multiplet, cyclohexyl CH ),. (overlapping multiplet, cyclohexyl CH ),. (overlapping multiplet, =CH-CH ),. (overlapping multiplet, cyclohexyl CH ), 0. (d, J =. Hz, H: CH-CH ). Minor Diastereomer: δ. (overlapping multiplet, =CH-CH),. (overlapping multiplet, =CH-CH ),. (m, H: CH-CH ),. (overlapping multiplet, cyclohexyl CH ),. (m, H: (C=O)CH),. (overlapping multiplet, cyclohexyl CH ),. (overlapping multiplet, cyclohexyl CH ),. (overlapping multiplet, =CH-CH ),. (overlapping multiplet, cyclohexyl CH ), 0. (d, J =. Hz, H: CH-CH ). C NMR ( MHz, CDCl ) Major Diastereomer: δ.0 (C=O),. (=CH-CH),. (=CH-CH ),. ((C=O)CH),. (.) (cyclohexyl CH ),. (CH-CH ),. (.) (cyclohexyl CH ),. (.) (cyclohexyl CH ),.0 (.) (cyclohexyl CH ),. (CH-CH ),. (=CH-CH ). Minor Diastereomer: δ. (C=O),. (=CH-CH),. (=CH-CH ),. ((C=O)CH),. (.) (cyclohexyl CH ),. (CH-CH ),. (.) (cyclohexyl CH ),.0 (.) (cyclohexyl CH ),. (.) (cyclohexyl CH ),. (=CH-CH ),.00 (CH-CH ). IR (CDCl ): ν max 00,. HRMS calcd for C H O [M+H]., found.. GC (Chiraldex B-TA : Hold 0 o C for min., ramp o C/min to o C) Major Diastereomer: t r =.,. min. Minor Diastereomer: t r =.,. min. O h S-0
11 h clear oil: H NMR (00 MHz, CDCl ) δ. (m, H: arom H),. (d, J = Hz, H: arom H),. (m, H: =CH),. (d, J = Hz, H: =CH(H) cis ),. (d, J = Hz, H: =CH(H) trans ),. (s, H: CH -Ph),. (dd, J = Hz, Hz, H: diastereotopic CH - CH=),. (dd, J = Hz, Hz, H: diastereotopic CH -CH=),. (s, H: (C=O)-CH ),. (m, H: CH -CH ), 0.0 (t, J = Hz, H: CH -CH ). C NMR ( MHz, CDCl ) δ.0 (C=O),.0 (arom. C),.0 (=CH), 0. (arom. CH),. (arom. CH), 00 0 S-
12 . (arom. CH),. (=CH ),. (C),. (CH -Ph),. (CH =CH-CH ),. ((C=O)-CH ),. (CH -CH ),.(CH -CH ). IR (CDCl ): ν max,,,. HRMS calcd for C H O [M+H]., found.0. i O 0 S-
13 00 0 i clear oil: H NMR (00 MHz, CDCl ) δ. (m, H: arom H),.0 (m, H: arom H),. (m, H: arom H),. (m, H: =CH),. (m, H: =CH),.0 (s, H: CH -Ph),. (m, H: CH-CH=),. (d, J = Hz, H: (C=O)CH -CH),. (m, H: ambiguous CH ),. (m, H: ambiguous diastereotopic CH ),. (m, H: ambiguous diastereotopic CH ),. (m, H: ambiguous diastereotopic CH ),. (m, H: ambiguous diastereotopic CH ). C NMR ( MHz, CDCl ) δ 0.0 (C=O),. (arom. C), 0. (.) (=CH),. (arom. CH),. (arom. CH),. (.) (=CH),. (arom. CH),. (CH -Ph),.0 ((C=O)CH -CH),. (CH-CH=),.0 (.,.) (ambiguous CH ),. (.) (ambiguous CH ),. (.,.) (ambiguous CH ). IR (CDCl ): ν max 0,,. HRMS calcd for C H O [M+H]., found.. HPLC (Diacel Chiralpak AD : : Hex:IPA, 0. ml/min ) t r =.0,. min O j House, H.; Fischer, W.; Gall, M.; McLaughlin, T.; Peet, N. J. Org. Chem.,, -. S-
14 j clear oil: H NMR (00 MHz, CDCl ) δ. (m, H: =CH),.0 (m, H: =CH),. (m, H: =CH-CH),. (app. pen, J = Hz, H: (CH ) -CH),. (d, J = Hz, H: (C=O)CH ),. (m, H: ambiguous CH ),. (m, H: ambiguous diastereotopic CH ),. (m, H: ambiguous diastereotopic CH ),. (m, H: ambiguous S-
15 diastereotopic CH ),.0 (m, H: ambiguous diastereotopic CH ),. (d, J = Hz, H: (CH ) ). C NMR ( MHz, CDCl ) δ. (C=O),. (.0) (=CH),. (.) (=CH),.0 ((C=O)CH ),. ((CH ) -CH),. (CH-CH=),. (.,.0) (ambiguous CH ),. (.) (ambiguous CH ),. (.,.) (ambiguous CH ),. ((CH ) ). IR (CDCl ): ν max 0,,. HPLC (Diacel Chiralpak AD :.: Hex:IPA, 0. ml/min ) t r =., 0. min. O k 0 S-
16 k 0 clear oil: H NMR (00 MHz, CDCl ) δ. (m, H: arom H),. (m, H: arom H),. (app. t, J = Hz, H: arom H),. (m, H: =CH),. (m, H: =CH),. (d, J = Hz, H: diastereotopic (C=O)CH ),. (d, J = Hz, H: diastereotopic (C=O)CH ),. (m, H: =CH-CH),.0 (m, H: ambiguous CH ),. (m, H: ambiguous diastereotopic CH ),. (m, H: ambiguous diastereotopic CH ),. (m, H: ambiguous diastereotopic CH ),. (m, H: ambiguous diastereotopic CH ). C NMR ( MHz, CDCl ) δ 00.0 (C=O),. (arom. C),. (arom. CH),. (.) (=CH),. (arom. CH),. (arom. CH),. (.) (=CH),. ((C=O)CH ),.0 (CH-CH=),. (.,.) (ambiguous CH ),. (.0) (ambiguous CH ),.0 (.,.) (ambiguous CH ). IR (CDCl ): ν max,,. HRMS calcd for C H O [M+H] 0., found 0.. HPLC (Diacel Chiralpak AD : : Hex:IPA, 0. ml/min ) t r =.,.0 min. l O 0 Fernandez-Mateos, A; Alonso, J.; Gonzalez, R. Tetrahedron.,, -0. S-
17 l clear oil: H NMR (00 MHz, CDCl ) δ. (m, H: =CH),. (m, H: =CH),. (m, H: CH-CH=),. (dd, J = Hz,. Hz, H: diastereotopic (C=O)CH ),. (overlapping multiplet, H: diastereotopic (C=O)CH ),. (overlapping multiplet, H: CH -CH ),. (m, H: ambiguous CH ),. (m, H: ambiguous diastereotopic CH ), S-
18 . (m, H: ambiguous diastereotopic CH ),.0 (t, J =. Hz, H: CH ). C NMR ( MHz, CDCl ) δ. (C=O),. (.) (=CH),. (.) (=CH),. ((C=O)CH ),. (CH-CH=),.0 (CH -CH ),. (.) (ambiguous CH ), 0. (.) (ambiguous CH ),. (CH ). IR (CDCl ): ν max 0, 0,. HRMS calcd for C H O [M+H]., found.00. GC (Chiraldex B-TA : Hold 0 o C for min., ramp 0. o C/min to o C) t r = 0.,. min. S-
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