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[3+2] Cycloaddition of Alkynyl Boronates and in situ Generated Azomethine Ylide

Chemistry 2023, e202303504

DOI: 10.1002/chem.202303504

Liashuk O.; Ryzhov I.; Hryshchuk O.; Volovenko Y.; Grygorenko O.

Scalable [3+2] cycloaddition of alkynyl boronates and in situ generated unstabilized azomethine ylide is reported for the first time. The selective formation of either 1 : 1 or 1 : 2 cycloaddition products was achieved by carefully optimizing the reaction conditions, mainly by controlling the reactant stoichiometry, catalyst loading, and internal temperature. The developed protocol tolerated many valuable functional groups, including TMS, protected alcohol (as ether or THP derivatives), or aldehyde (as acetal). Further common C−C and C−heteroatom bond-forming reactions, as well as scaled-up procedures demonstrate the utility of the prepared compounds as building blocks for organic synthesis and drug discovery.

[3+2] Cycloaddition of Alkynyl Boronates and in situ Generated Azomethine Ylide

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