Traceless Protection for More Broadly Applicable Olefin Metathesis.

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ID: 33355
2019
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Abstract
An operationally simple in situ protection/deprotection strategy that significantly expands the scope of kinetically controlled catalytic Z- and E-selective olefin metathesis is introduced. Prior to the addition of a sensitive Mo- or Ru-based complex, treatment of a hydroxy- or a carboxylic-acid-containing olefin with commercially available HB(pin) or readily accessible HB(trip) (pin=pinacolato, trip=2,4,6-tri(isopropyl)phenyl) for 15 min is sufficient for efficient generation of a desired product. Routine workup leads to quantitative deprotection. A range of stereochemically defined Z- and E-alkenyl chlorides, bromides, fluorides, and boronates or Z-trifluoromethyl-substituted alkenes with a hydroxy or carboxylic acid group were thus prepared in 51-97 % yield with 93 to >98 % stereoselectivity. We also show that, regardless of whether a polar functional unit is present or not, a small amount of HB(pin) may be used to remove residual water, significantly enhancing efficiency.
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mu2019tracelessangewandte Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Yucheng Mu, Thach T Nguyen, Farid W van der Mei, Richard R Schrock, Amir H Hoveyda
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Journal angewandte chemie (international ed in english)
Year 2019
DOI
10.1002/anie.201901132
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