Bicyclo[1.1.1]pentane‐Derived Building Blocks for Click Chemistry. Issue 43 (23rd November 2017)

• Record Type: Journal Article
• Authors: Kokhan, Serhii O.; Valter, Yevheniia B.; Tymtsunik, Andriy V.; Komarov, Igor V.; Grygorenko, Oleksandr O.
• Is Part Of: European journal of organic chemistry. Issue 43(2017)
• Page Start: 6450
• Page End: 6456
• Publication Date: 2017-11-23
• Subjects: Alkynes -- Azides -- Nitrogen heterocycles -- Click chemistry -- Propellane -- Cage compounds; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701296
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Syntheses of bicyclo[1.1.1]pentane‐derived azides and terminal alkynes – interesting substrates for click reactions – are described. With a few exceptions, these compounds were prepared in two or three steps starting from common synthetic intermediates – the corresponding carboxylic acids. The key step in the synthesis of 1‐azidobicyclo[1.1.1]pentanes is a copper‐catalysed diazo‐transfer reaction with imidazole‐1‐sulfonyl azide. The preparation of bicyclo[1.1.1]pentyl‐substituted alkynes relies on a Seyferth–Gilbert homologation with dimethyl 1‐diazo‐2‐oxopropylphosphonate (Ohira–Bestmann reagent). Both types of target compounds were found to be suitable substrates for click reactions, and thus they are promising building blocks for medicinal, combinatorial and bioconjugate chemistry. A practically important side result of this study was a multigram preparation of Boc‐monoprotected 1, 3‐diaminobicyclo[1.1.1]pentane – a representative bicyclic conformationally restricted diamine derivative. Abstract : Syntheses of mono‐ and bifunctional bicyclo[1.1.1]pentane‐derived azides and terminal alkynes – promising building blocks for medicinal, combinatorial, and bioconjugate chemistry – are described. The utility of the title products as substrates for copper‐catalysed click reactions is also demonstrated.