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Abstract
The reaction of bicyclo[1.1.0]butyl pinacol boronic ester (BCB‐Bpin) with nucleophiles has been studied. Unlike BCBs bearing electron‐withdrawing groups, which react with nucleophiles at the β‐position, BCB‐Bpin reacts with a diverse set of heteroatom (O, S, N)‐centred nucleophiles exclusively at the α‐position. Aliphatic alcohols, phenols, carboxylic acids, thiols and sulfonamides were found to be competent nucleophiles, providing ready access to α‐heteroatom‐substituted cyclobutyl boronic esters. In contrast, sterically hindered bis‐sulfonamides and related nucleophiles reacted with BCB‐Bpin at the β’‐position leading to cyclopropanes with high trans‐selectivity. The origin of selectivity is discussed.
Original language | English |
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Pages (from-to) | 212-216 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 60 |
Issue number | 1 |
Early online date | 21 Sept 2020 |
DOIs | |
Publication status | Published - 22 Dec 2020 |
Keywords
- 1,2-migration
- boronic esters
- cyclobutane
- cyclopropane
- strain release
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Dive into the research topics of 'α‐Selective Ring‐Opening Reactions of Bicyclo[1.1.0]butyl Boronic Ester with Nucleophiles'. Together they form a unique fingerprint.Projects
- 1 Finished
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Modular approach to structurally diverse four-membered (spiro)cycles using highly strained precursors
Aggarwal, V. K. (Principal Investigator)
1/04/19 → 30/09/23
Project: Research