Enantiospecific, Regioselective Cross-Coupling Reactions of Secondary Allylic Boronic Esters

An original­ syn: The first enantioselective Suzuki–Miyaura cross‐coupling of chiral, enantioenriched secondary allylic boronic esters is described (see scheme; DME=dimethoxyethane, Bpin = pinacolboryl, dba = dibenzylideneacetone). Mechanistic studies show that the reactions proceed via γ‐selective...

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Bibliographic Details
Published in:Chemistry : a European journal 2013-12, Vol.19 (52), p.17698-17701
Main Authors: Chausset-Boissarie, Laetitia, Ghozati, Kazem, LaBine, Emily, Chen, Jack L.-Y., Aggarwal, Varinder K., Crudden, Cathleen M.
Format: Article
Language:English
Subjects:
allylboronate
Boron - chemistry
Catalysis
Chemical reactions
Chemistry
Cross coupling
Esters
Esters - chemistry
Palladium
Pathways
Stereoisomerism
stereospecificity
Suzuki-Miyaura
synthetic methods
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Summary:An original­ syn: The first enantioselective Suzuki–Miyaura cross‐coupling of chiral, enantioenriched secondary allylic boronic esters is described (see scheme; DME=dimethoxyethane, Bpin = pinacolboryl, dba = dibenzylideneacetone). Mechanistic studies show that the reactions proceed via γ‐selective transmetalation followed by reductive elimination. The reaction provides the first independent confirmation that the transmetalation of boronic esters proceeds via a syn pathway.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201303683