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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Bistrimethylsilylpropargylic ether: a versatile ambident synthon to access substituted allenyne ethers and
Maude Brossat1, Marie-Pierre Heck, Charles Mioskowski
1CEA-Saclay, iBiTec-S, Service de Chimie Bioorganique et de Marquage, Bât 547, F-91191 Gif sur Yvette cedex, France.
Abstract:
The reactivity of 1,5-bis(trimethylsilyl)propargylic ethers 3 toward bases and electrophiles was investigated. Bispropargylic ethers 4, substituted allenyne ethers 6-8, and alpha-substituted bispropargylic ethers 9 were prepared in good yields, respectively, by protodesilylation, isomerization, or metalation/alkylation of bispropargylic protected alcohol 3. The ambident behavior of metalated synthon 3 was discussed and rationalized. Removal of the protecting groups of 9 easily afforded useful alpha-substituted bispropargylic alcohol.
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