A General Method for Synthesis of Unclosed Cryptands via H-Bond Templated Macrocyclization and Subsequent Mild Postfunctionalization | Zendy

Kajetan Dąbrowa | Zendy; Patryk Niedbała | Zendy; Maciej Majdecki | Zendy; Piotr Duszewski | Zendy; Janusz Jurczak | Zendy

Open Access

A General Method for Synthesis of Unclosed Cryptands via H-Bond Templated Macrocyclization and Subsequent Mild Postfunctionalization

Author(s) -

Kajetan Dąbrowa,

Patryk Niedbała,

Maciej Majdecki,

Piotr Duszewski,

Janusz Jurczak

Publication year - 2015

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.5b02324

Subject(s) - chemistry , cryptand , intramolecular force , yield (engineering) , amide , combinatorial chemistry , chloride , catenane , computational chemistry , stereochemistry , ion , molecule , organic chemistry , materials science , metallurgy

A practical four-step synthesis of a model 26-membered N-Boc-protected macrocycle, starting from commercially available and inexpensive materials, is reported. The crucial macrocyclization step does not require high-dilution conditions and is completed in a short time (8 h). The high yield of macrocyclization (61%) is achieved owing to templation by intramolecular H-bonds and a chloride anion, which both help to adopt a favorable folded conformation of the open-chain intermediate. Finally, mild, selective, and efficient incorporation of intraannular amide function leading to five diversely functionalized unclosed cryptands (UCs) is described.

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