Supporting information. Double Reformatsky Reaction: Divergent Synthesis of δ-hydroxy-β-ketoesters

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1 Supporting information Double Reformatsky Reaction: Divergent Synthesis of δ-hydroxy-β-ketoesters Masahiro Mineno,* Yasuhiro Sawai, Kazuaki Kanno, Naotaka Sawada and Hideya Mizufune Chemical Development Laboratories, CMC Center, Takeda Pharmaceutical Company Limited, Osaka , Japan Contents Low-level metal impurities The amount of Reformatsky reagent Details of X-ray single crystal structure analysis of zinc complex of 3a ethanol solvate S2 S3 S4 1 H and 13 C NMR spectra of δ-hydroxy-β-ketoesters S6 1 H NMR, 13 C NMR, HMBC and HMQC spectra of zinc complex of 3a THF solvate S28 1 H NMR and 13 C NMR spectra of zinc complex of 3a ethanol solvate S32 S1

2 Low-level metal impurities Zinc mediated Simmons-Smith reaction is known to be affected by a quite low amount of lead. 1 It is generally known that there are two types of zinc metal preparations; one is electrolytic zinc, and the other is distilled zinc. Distilled zinc is generally more likely to contain lead than electrolytic zinc. To see if the residual metal affects the reactivity or not, we evaluated the reactivity with several different zincs, which were prepared by several suppliers and in different ways. As shown in Table S-1, there was no relationship between the reactivity and the residual metals. Table S-1. The effect of low-level metal impurities on double Reformatsky reaction Run Supplier Purification method Component (%) Zn Pb Cd Fe Conversion (3a, %) a 1 A Distilled B Distilled B Electrolytic > a Determined by HPLC S2

3 The amount of Reformatsky reagent The effect of various amounts of Reformatsky reagent on the reactivity was evaluated (Table S-2). The study was performed at room temperature without additives. Theoretically, this reaction can be completed by the use of 2 equiv of Reformatsky reagent. However, 2 equiv of Reformatsky reagent only afforded a small amount of double Reformatsky product 3b (Run 2). The lower conversions do not appear to be due to self-condensation of the Reformatsky reagent, since self-condensed Reformatsky reagents were hardly detected during this study (checked by GC). The conversion could be improved by increasing the amount of Reformatsky reagent (Runs 3 and 4). Table S-2. The effect of various amounts of Reformatsky reagent on double Reformatsky reaction Run Equiv of Reformatsky reagent Ratio (1b/2b/3b) a /1/ /90/ /84/ /52/48 a Determined by HPLC analysis. S3

4 Details of X-ray single crystal structure analysis of zinc complex of 3a ethanol solvate Crystal data for the zinc complex of 3a ethanol solvate [Zn 3 (C 18 H 17 NO 4 ) 2 Br 2 (C 2 H 5 OH)] C 2 H 5 OH, MW = ; crystal size, 0.20 x 0.17 x 0.10 mm; colorless, block; monoclinic, space group P2 1 /c, a = (3) Å, b = (3) Å, c = (4) Å, α = γ = 90, β = (8) V = (3) Å 3, Z = 4, Dx = g/cm 3, T = 100 K, µ = mm -1, λ = Å, R 1 = 0.045, wr 2 = The crystal data for the zinc complex of 3a ethanol solvate was obtained by crystallization from ethanol/acetone solution. All measurements were made on a Rigaku R-AXIS RAPID diffractometer using graphite monochromated Cu-Kα radiation. The structure was solved by direct methods with SHELXS-97 2 and was refined using full-matrix least-squares on F 2 with SHELXL All non-h atoms were refined with anisotropic displacement parameters. CCDC contains all crystallographic data of this publication and is available free of charge at The Cambridge Crystallographic Data Centre via N O O O 44 O Br Zn O Zn Zn Br O 17O 14O 3 N O Figure S-1. ORTEP of the Zinc Complex of 3a ethanol solvate, thermal ellipsoids are drawn at 20% probability level. S4

5 Table S-3. Bond Length for the Zinc Complex of 3a ethanol solvate Atom Atom Distance (Å) Atom Atom Distance (Å) C1 C (6) C1 C (6) C1 O (5) C1 C (5) C2 N (5) C2 C (6) N3 C (6) N3 Zn (4) C4 C (7) C5 C (6) C6 C (6) C8 C (6) C8 C (6) C9 C (7) C10 C (7) C11 C (7) C12 C (7) O14 Zn (3) O14 Zn (3) C15 C (7) C16 O (5) C16 C (7) O17 Zn (3) O17 Zn (3) C18 C (7) C19 O (6) C19 O (6) O20 Zn (4) O21 C (7) C22 C (7) C24 C (7) C24 C (6) C24 O (5) C24 C (5) C25 N (5) C25 C (6) N26 C (7) N26 Zn (4) C27 C (6) C28 C (6) C29 C (7) C31 C (5) C31 C (6) C32 C (6) C33 C (7) C34 C (6) C35 C (6) O37 Zn (3) O37 Zn (3) C38 C (6) C39 O (5) C39 C (5) O40 Zn (3) O40 Zn (3) C41 C (6) C42 O (5) C42 O (4) O43 Zn (3) O44 C (5) C45 C (6) Zn47 O (4) Zn48 Br (7) Zn50 Br (6) O52 C (6) C53 C (7) References cited in the Supporting Information 1. A catalytic amount of lead promotes further reduction of zinc carbenoid with zinc in THF to give the geminal dizinc compound (CH 2 (ZnI) 2 ) ; (a) Matsubara, S.; Oshima, K.; Matsuoka, H.; Matsumoto, K.; Ishikawa, K.; Matsubara, E. Chem. Lett. 2005, 34, 952. (b) Matsubara, S.; Oshima, K.; Utimoto, K. J. Organomet. Chem. 2001, 617, 767. (c) Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem.1994, 59, Sheldrick, G.M. Acta Cryst. A, 2008, 64, 112. S5

6 Ethyl 5-hydroxy-3-oxo-5-phenyl-5-(pyridin-2-yl)pentanoate (3a): 1 H NMR (500 MHz) DMSO-d 6 S6

7 Ethyl 5-hydroxy-3-oxo-5-phenyl-5-(pyridin-2-yl)pentanoate (3a): 13 C NMR (125 MHz) DMSO-d 6 S7

8 Ethyl 5-hydroxy-3-oxo-5, 5-diphenylpentanoate (3b): 1 H NMR (500 MHz) DMSO-d 6 S8

9 Ethyl 5-hydroxy-3-oxo-5, 5-diphenylpentanoate (3b): 13 C NMR (125 MHz) DMSO-d 6 S9

10 Ethyl 5, 5-bis(4-fluorophenyl)-5-hydroxy-3-oxopentanoate (3e): 1 H NMR (500 MHz) CDCl 3 S10

11 Ethyl 5, 5-bis(4-fluorophenyl)-5-hydroxy-3-oxopentanoate (3e): 13 C NMR (125 MHz) CDCl 3 S11

12 Ethyl 5-hydroxy-5, 5-bis(4-methoxyphenyl)-3-oxo pentanoate (3f): 1 H NMR (500 MHz) CDCl 3 S12

13 Ethyl 5-hydroxy-5, 5-bis(4-methoxyphenyl)-3-oxo pentanoate (3f): 13 C NMR (125 MHz) CDCl 3 S13

14 Diethyl 5,5'-(1,4-phenylene)bis(5-hydroxy-3-oxopentanoate) (6g): 1 H NMR (500 MHz) CDCl 3 S14

15 Diethyl 5,5'-(1,4-phenylene)bis(5-hydroxy-3-oxopentanoate) (6g): 13 C NMR (125 MHz) CDCl 3 S15

16 Methyl 4-(5-ethoxy-1-hydroxy-3, 5-dioxopentyl) benzoate (6h): 1 H NMR (500 MHz) CDCl 3 S16

17 Methyl 4-(5-ethoxy-1-hydroxy-3, 5-dioxopentyl)benzoate (6h): 13 C NMR (125 MHz) CDCl 3 S17

18 Ethyl 5-hydroxy-5-(4-nitrophenyl)-3-oxopentanoate (6i): 1 H NMR (500 MHz) CDCl 3 S18

19 Ethyl 5-hydroxy-5-(4-nitrophenyl)-3-oxopentanoate (6i): 13 C NMR (125 MHz) CDCl 3 S19

20 Ethyl 5-(4-bromophenyl)-5-hydroxy-3-oxopentanoate (6j): 1 H NMR (500 MHz) CDCl 3 S20

21 Ethyl 5-(4-bromophenyl)-5-hydroxy-3-oxopentanoate (6j): 13 C NMR (125 MHz) CDCl 3 S21

22 Ethyl 5-hydroxy-3-oxo-5-(thiophen-3-yl)pentanoate (6k): 1 H NMR (500 MHz) CDCl 3 S22

23 Ethyl 5-hydroxy-3-oxo-5-(thiophen-3-yl)pentanoate (6k): 13 C NMR (125 MHz) CDCl 3 S23

24 Ethyl-(6E)-5-hydroxy-3-oxo-7-phenylhept-6-enoate (6l): 1 H NMR (500 MHz) CDCl 3 S24

25 Ethyl-(6E)-5-hydroxy-3-oxo-7-phenylhept-6-enoate (6l): 13 C NMR (125 MHz) CDCl 3 S25

26 Ethyl 5-hydroxy-3-oxo-7-phenylheptanoate (6m): 1 H NMR (500 MHz) CDCl 3 S26

27 Ethyl 5-hydroxy-3-oxo-7-phenylheptanoate (6m): 13 C NMR (125 MHz) CDCl 3 S27

28 Zinc complex of 3a THF solvate: 1 H NMR (500 MHz) DMSO-d 6 S28

29 Zinc complex of 3a THF solvate: 13 C NMR (125 MHz) DMSO-d 6 S29

30 Zinc complex of 3a THF solvate: HMBC DMSO-d 6 S30

31 Zinc complex of 3a THF solvate: HMQC DMSO-d 6 S31

32 Zinc complex of 3a ethanol solvate: 1 H NMR (500 MHz) DMSO-d 6 S32

33 Zinc complex of 3a ethanol solvate: 13 C NMR (125 MHz) DMSO-d 6 S33

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