Manuscript Title Goes Here (Word Style “RGC Manuscript Title”).

Author Names (Word Style “RGC Authors”).

Department of Chemistry, Oregon State University, Corvallis, OR 97331

Electronic Supplementary Information: Experimental

General. Infrared spectra were recorded neat unless otherwise indicated and are reported in cm-1. 1H NMR spectra were recorded in deuterated solvents and are reported in ppm relative to tetramethylsilane and referenced internally to the residually protonated solvent. 13C NMR spectra were recorded in deuterated solvents and are reported in ppm relative to tetramethylsilane and referenced internally to the residually protonated solvent.

Routine monitoring of reactions was performed using EM Science DC-Alufolien silica gel, aluminum-backed TLC plates. Flash chromatography was performed with the indicated eluents on EM Science Gedurian 230-400 mesh silica gel.

Air and/or moisture sensitive reactions were performed under usual inert atmosphere conditions. Reactions requiring anhydrous conditions were performed under a blanket of argon, in glassware dried in an oven at 120°C or by flame, then cooled under argon. Dry THF and DCM were obtained via a solvent purification system. All other solvents and commercially available reagents were either purified via literature procedures or used without further purification.

Alcohol 2. (Name and compound number in bold) To a stirred solution of ketone 1 (##.# g, ##.# mmol) in solvent A (## mL) at -78°C was added sequentially reagent A (##.# g, ##.# mL, ##.# mmol) and reagent B (##.# mL, ##.# mmol, #.# M in solvent B). After ## min, the reaction was warmed to rt. After ## min, the reaction was quenched by sat. aq. reagent C (## mL) and extracted with solvent C (3 X ## mL). The dried (MgSO4 or NaSO4) extract was concentrated in vacuo purified by chromatography over silica gel, eluting with ##-##% EtOAc / hexanes, to give 2 (##.# g, ##.# mmol, ##%) as a white solid. [α]D23 = +#.#° (c = #.#, solvent); Mp ###-###ºC; IR (neat) ####, ####, #### cm-1; 1H NMR (### MHz, deuterated solvent) δ #.## (multiplicity, J = ##, ## Hz, #H), #.##-#.## (m, #H) ppm; 13C NMR (## MHz, deuterated solvent) δ ###.#, ###.# ppm; HRMS (type of ionization) calcd. for CmHnNoOp (portion of structure – typically M+ or M+H) ###.####, found ###.####. (ABC I-11)

Alcohol 3. (Name and compound number in bold) To a stirred solution of alcohol 2 (##.# g, ##.# mmol) in solvent A (## mL) at -78°C was added sequentially reagent A (##.# g, ##.# mL, ##.# mmol) and reagent B (##.# mL, ##.# mmol, #.# M in solvent B). After ## min, the reaction was warmed to rt. After ## min, the reaction was quenched by sat. aq. reagent C (## mL) and extracted with solvent C (3 X ## mL). The dried (MgSO4 or NaSO4) extract was concentrated in vacuo purified by chromatography over silica gel, eluting with ##-##% EtOAc / hexanes, to give 3 (##.# g, ##.# mmol, ##%) as a white solid. [α]D23 = +##.#° (c = #.#, solvent); Mp ###-###ºC; IR (neat) ####, ####, #### cm-1; 1H NMR (### MHz, deuterated solvent) δ #.## (multiplicity, J = ##, ## Hz, #H), #.##-#.## (m, #H) ppm; 13C NMR (## MHz, deuterated solvent) δ ###.#, ###.# ppm; HRMS (type of ionization method used) calcd. for CmHnNoOp (typically M+ or M+H) ###.####, found ###.####. (ABC V-34)

(Delete after reading): Experimentals must follow the standard format. All neat liquids are reported (mass, volume, moles). All solutions are reported (volume, moles, molarity of solution in solvent). All solids are reported as (mass, moles). All solvents are reported as (volume). All products are reported (mass, moles, yield). Spectra data must be listed in the order shown above. Delete any characterization method not applicable. All new compounds must contain [α]D23 (if enantioenriched), Mp (if solid), IR, 1H NMR, 13C NMR and HRMS. All literature (known) compounds must contain 1H NMR and 13C NMR data as well as reference citing the preparation of known compound (in ACS format). Footnote / Endnotes containing a brief experimental procedure may also be used for preparation of “in situ” reagents (e.g. LDA, LiDBB) used in an experiment.

(Delete after reading): Optical rotations are typically reported to tenths of degree and concentrations are reported to tenths of degree (remember: c = 1.0 is 10 mg / mL). Melting points are typically reported as ranges of to the single units of °C listed as the temperature at which the sample started to melt until the temperature the sample completed melting. IR spectra are reported to the single units of cm-1 with typically 5-10 key stretches included in an experimental starting from the largest number first. 1H NMR are typically reported in as the single mid point of signal for discernable individual signals or as a range for signals (or groups of signals) that can not be either well-distinquished or assigned a clear multiplicity. In either case, the units are reported to the hundreds of ppm listed from largest number first (Ranges are listed reported with low number then high number, e.g. 4.56-4.62). In the case of clearly defined coupling constants, those are reported to the tenths of Hz. 13C NMR are typically reported to tenths of ppm starting from the largest number first. High Res Mass Spec data is typically reported to four digits after the decimal place. The molecular formula used is typically the mass ion (M+), mass ion plus hydrogen (M+H) or the mass ion plus a Group I metal (M+Na). The error in the calculated and observed numbers MUST be less than 10 ppm – preferable less than 5 ppm. Labbook codes are reported at end of experimental procedures as your initials, roman numerals for labbook number and regular numbers for page number (e.g. ABC VI-43. All spectra should be saved in IDENTICAL file names formats.

References

. Format references using standard ACS Format with first and last page numbers. Example: Yang, H.; Carter, Rich, G. J. Org. Chem. 2009, 75, 5151-5156.

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Manuscript Title Goes Here (Word Style “RGC Manuscript Title”)

Rich Carter

2011-11-11

Oregon State University