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Synthesis of Alkenylboronic Esters: An Alternative Route to Trisubstituted Homoallylic Alcohols
Author(s) -
Gehrke Yvonne,
Berg Christina Annette,
Vahabi Roza,
Pietruszka Jörg
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600139
Subject(s) - stereocenter , chemistry , moiety , stereoselectivity , yield (engineering) , coupling reaction , double bond , organic chemistry , stereochemistry , enantioselective synthesis , catalysis , materials science , metallurgy
New alkenylboronic esters were synthesised from halo‐substituted alkenylboronic esters through cross‐coupling reactions. Upon Johnson rearrangement, enantiomerically pure allylboronates bearing a stereogenic centre in the position α to the boron moiety were obtained in moderate yield (53 %; 29 % over six steps from the protected propargylic alcohols). The products of these reactions were separable by medium‐pressure liquid chromatography, and could be used in highly stereoselective allylation reactions to synthesise enantiomerically enriched homoallylic alcohols containing a 1,1,2‐trisubstituted ( Z )‐configured double bond.