Restriction lift date: 2029-12-31
Rhodium catalysed 1,4-addition of N-Boc-indol-3-ylboronic acid to α,β-unsaturated carbonyls
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Date
2024
Authors
O'Driscoll, Conor C.
Journal Title
Journal ISSN
Volume Title
Publisher
University College Cork
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Abstract
In recent years, work within the McGlacken group has focused on the asymmetric conjugate additions of indole boronic acids. The work presented in this thesis is concerned with the exploration of the asymmetric rhodium-catalysed conjugate addition of indol-3-ylboronic acids to α,β-unsaturated carbonyl compounds. Optimisation studies towards the asymmetric addition of N-Boc-indol-3-ylboronic acid to 2-cyclohexen-1-one are described herein. With the optimised reaction conditions, a variety of substrates was explored and the synthesis of a number of novel compounds is described. Modest yields of up to 39% were achieved, with excellent enantioselectivities of up to 96%.
Description
Keywords
Rhodium , Asymmetric catalysis , Boronic acid , Conjugate addition
Citation
O'Driscoll, C. C. 2024. Rhodium catalysed 1,4-addition of N-Boc-indol-3-ylboronic acid to α,β-unsaturated carbonyls. MRes Thesis, University College Cork.