Catalytic asymmetric olefin metathesis

Colell, Angus W. Logan, Zijian Zhou, Roman V. Shchepin, Danila A. Barskiy, Gerardo X. Ortiz Jr. Chekmenev, Warren S. Warren, Thomas Theis J. Logan, Thomas Theis, Johannes F. Colell, Warren S. Ortiz, Angus W. Logan, Kevin E. Claytor, Yesu Feng, William P. Huhn, Volker Blum, Steven J. Chekmenev, Qiu Wang, Warren S. Malcolmson, Travis S. Young, J.

Walsh PNAS, , , Crawford, Sarah A. Mahlstedt, Steven J. Malcolmson, Jon Clardy, Christopher T. Chem Biol , , 18 , — Bolla, Steven J. Malcolmson, Daniel Kahne, Neil L. Kelleher, Christopher T. Lichtscheidl, Victor W. Takase, Richard R.

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Schrock, Steven J. Malcolmson, Simon J. Meek, Bo Li, Elizabeth T. Kiesewetter, Amir H. Organometallics , , 31 , — Meek, Steven J. Malcolmson, Bo Li, Richard R. Schrock, Amir H. Sattely, Simon J. Malcolmson, Richard R. Malcolmson, Katherine S. Dunne, Simon J. Meek, Amber L. Thompson, Richard R.

Sattely, Richard R. Malcolmson, Alessandra Puglisi, Richard R. Malcolmson, Kangnan Li and Xinxin Shao. Synlett , , 30 , Hoveyda, R. Kashif M.

The asymmetric Schrock olefin metathesis catalysts. A computational study

Khan, Sebastian Torker, Steven J. Handbook of Olefin Metathesis, Vol. Walsh, Steven J. ACS Chem. Alcohols 23, 83, and 86 and substrates 38, 40, 48, 55, 60, and 66, were dried by azeotropic distillation with C 6 H 6 prior to use in reactions with Mo-based reagents.


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Substrates 40 and 46 were dried by distillation from Na prior to use in reactions with Mo reagents. Substrates 60, 38, 40, 44, 46, 48, 55, and 66 were synthesized according to previously reported procedures e. Sattely, Ph. Thesis , Boston College, ; S. Dolman, et al, J. Sattely et al. Kiely et al. Bands are characterized as broad br , strong s , medium m , or weak w. Melting points were measured on a Thomas Hoover capillary melting point apparatus and are uncorrected.

Baker were passed successively through activated Cu and alumina columns. Tetrahydrofuran Aldrich was distilled from sodium benzophenone ketyl. Mo-based bis alkoxide complexes 50 and 62a-c, 63, and 20 were prepared according to published procedures e. Schrock et al. Mo-bis pyrrolide complexes 22a-b were prepared according to published procedures e. Mo-monoalkoxide-monopyrrolide complex rac-9 was prepared according to published procedures e.


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Mo complexes were handled under an inert atmosphere in a dry box. Ru-based complex 65a was obtained from Materia, Inc. Ru-based complex 65b was purchased from Materia and used as received. Ru-based complex 4a was prepared according to published procedures e. Ru-based complexes were handled under an inert atmosphere in a dry box for comparison purposes. R -binol was purchased from Kankyo Kakagu Center, Co. Bromine was purchased from Acros and distilled from P 2 O 5 prior to use.

Chloromethyl methyl ether was purchased from Aldrich and used as received. Hexachloroethane was purchased from Alfa Aesar and recrystallized from ethanol, then dried by azeotropic distillation with C 6 H 6 , prior to use. Hydrogen chloride 4. Platinum IV oxide was purchased from Aldrich and used as received. Potassium carbonate was purchased from Fisher and used as received. Sodium bisulfite was purchased from Fisher and used as received. Triethylamine was purchased from Aldrich and distilled from CaH 2 prior to use. All ligands were prepared from enantiomerically pure R -binol.

EPA2 - Novel methods for cross-metathesis of terminal olefins - Google Patents

Jpn, , 61, See FIG. The layers were partitioned. The combined organic layers were dried over MgSO 4 , filtered, and concentrated.


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  7. The resulting yellow foam was purified by silica gel chromatography dry load method, petroleum ether:Et 2 O to afford 23 mg, 0. A mL round-bottom flask equipped with magnetic stir bar was charged with diol 81 5. Bromine 1. After 20 min, the reaction was quenched by the slow addition of a saturated aqueous solution of NaHSO 3 mL. The resulting brown solid was passed through a short plug of silica gel eluted with CH 2 Cl 2 to afford 82 6. A mL round-bottom flask containing a magnetic stir bar was charged with diol 82 3.

    At this time, the mixture was diluted with a saturated aqueous solution of NaHCO 3 mL and the layers were partitioned. The suspension was filtered while cold and dried under reduced pressure to afford 83 2.

    A solution of diol 82 1. After 3 h, the reaction was quenched by the addition of H 2 O 10 mL.

    The resulting yellow oil was purified by silica gel column chromatography petroleum ether:Et 2 O to afford 84 1. A mL round-bottom flask with magnetic stir bar was charged with bis methoxymethyl ether 84 mg, 1. A solution of hexachloroethane mg, 3. The combined organic layers were washed with a saturated aqueous solution of NaCl 50 mL , dried over MgSO 4 , filtered, and concentrated.

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