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Traceless Protection for More Broadly Applicable Olefin Metathesis.
- Source :
-
Angewandte Chemie . 4/8/2019, Vol. 131 Issue 16, p5419-5424. 6p. - Publication Year :
- 2019
-
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)2 (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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 131
- Issue :
- 16
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 135668916
- Full Text :
- https://doi.org/10.1002/ange.201901132