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The Boron‐Wittig Olefination of Aldehydes and Ketones with Bis[(pinacolato)boryl]methane: an Extended Reaction Scope

2019; Wiley; Volume: 2019; Issue: 33 Linguagem: Inglês

10.1002/ejoc.201900648

1434-193X

Maksym Kovalenko, Dmytro V. Yarmoliuk, Dmytro Serhiichuk, Daria Chernenko, Vladyslav Smyrnov, Artur Breslavskyi, Oleksandr V. Hryshchuk, Ihor Kleban, Yuliya V. Rassukana, Andriy V. Tymtsunik, Andrey A. Tolmachev, Yuliya O. Kuchkovska, Oleksandr O. Grygorenko,

Advanced Synthetic Organic Chemistry

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.