Functionalisation of isoindolinones via a calcium catalysed Hosomi-Sakurai allylation

A rapid and functionally tolerant calcium catalysed Hosomi-Sakurai reaction has been realised. Employing 1 mol% calcium, allylated isoindolinones can be synthesised in high yields and the reaction is shown to be tolerant to a range of medicinally relevant functional groups including heterocycles. Th...

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Published inChemical communications (Cambridge, England) Vol. 55; no. 57; pp. 8317 - 8320
Main Authors Basson, Ashley J., McLaughlin, Mark G.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 11.07.2019
Royal Society of Chemistry
Subjects
Allyl compounds
Calcium
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Functional groups
Physical Sciences
Reaction mechanisms
Science & Technology
EFFICIENT SYNTHESIS
ISOINDOLIN-1-ONES
LACTAMS
ASYMMETRIC-SYNTHESIS
CYCLIZATION
RUCL2(=CHR)(PR)
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Summary:A rapid and functionally tolerant calcium catalysed Hosomi-Sakurai reaction has been realised. Employing 1 mol% calcium, allylated isoindolinones can be synthesised in high yields and the reaction is shown to be tolerant to a range of medicinally relevant functional groups including heterocycles. The synthetic utility of the reaction has been shown, and a plausible reaction mechanism is provided.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc02450f