α‐Selective Ring‐Opening Reactions of Bicyclo[1.1.0]butyl Boronic Ester with Nucleophiles

Research output: Contribution to journalArticle (Academic Journal)peer-review

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 languageEnglish
Pages (from-to)212-216
Number of pages5
JournalAngewandte Chemie - International Edition
Volume60
Issue number1
Early online date21 Sep 2020
DOIs
Publication statusPublished - 22 Dec 2020

Keywords

  • 1,2-migration
  • boronic esters
  • cyclobutane
  • cyclopropane
  • strain release

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