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The Boron‐Wittig Olefination of Aldehydes and Ketones with Bis[(pinacolato)boryl]methane: an Extended Reaction Scope
Author(s) -
Kovalenko Maksym,
Yarmoliuk Dmytro V.,
Serhiichuk Dmytro,
Chernenko Daria,
Smyrnov Vladyslav,
Breslavskyi Artur,
Hryshchuk Oleksandr V.,
Kleban Ihor,
Rassukana Yuliya,
Tymtsunik Andriy V.,
Tolmachev Andrey A.,
Kuchkovska Yuliya O.,
Grygorenko Oleksandr O.
Publication year - 2019
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.201900648
Subject(s) - wittig reaction , chemistry , steric effects , methane , boron , organic chemistry , substrate (aquarium) , electronic effect , organoboron compounds , boronic acid , oceanography , geology
Preparation of 2,2‐disubstituted and 2‐monosubstituted alkenylboronic acid esters from aliphatic and aromatic ketones and aldehydes by the boron‐Wittig olefination with bis[(pinacolato)boryl]methane was examined and applied on the multigram scale. The influence of the substrate steric and electronic features on the overall efficiency and stereochemical outcome of the reaction was studied. Additionally, a series of diversely functionalized (hetera)cycloalkylidenemethyl and (hetera)cycloalkyl boronic acid‐derived building blocks was synthesized.