Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 52287-51-1, is researched, SMILESS is BrC1=CC=C2OCCOC2=C1, Molecular C8H7BrO2Journal, Article, Research Support, N.I.H., Extramural, Research Support, U.S. Gov’t, Non-P.H.S., Journal of the American Chemical Society called Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination, Author is O’Connor, Thomas J.; Mai, Binh Khanh; Nafie, Jordan; Liu, Peng; Toste, F. Dean, the main research direction is axial chiral fluoroallene preparation; copper catalyst enantioselective fluoride elimination Josiphos ligand preparation; mol structure optimized chiral ferrocene phosphine propargyl difluoride DFT; silylation catalyst ferrocene chiral Josiphos propargylic difluoride stereoselective mechanism.Electric Literature of C8H7BrO2.
Herein we report the copper-catalyzed silylation of propargylic difluorides to generate axially chiral, tetrasubstituted monofluoroallenes in both good yields (27 examples >80%) and enantioselectivities (82-98% ee). Compared to previously reported synthetic routes to axially chiral allenes (ACAs) from prochiral substrates, a mechanistically distinct reaction has been developed: the enantiodiscrimination between enantiotopic fluorides to set an axial stereocenter. DFT calculations and vibrational CD (VCD) suggest that β-fluoride elimination from an alkenyl copper intermediate likely proceeds through a syn-β-fluoride elimination pathway rather than an anti-elimination pathway. The effects of the C1-sym. Josiphos-derived ligand on reactivity and enantioselectivity were investigated. Not only does this report showcase that alkenyl copper species (like their alkyl counterparts) can undergo β-fluoride elimination, but this elimination can be achieved in an enantioselective fashion.
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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics