title: Bistrimethylsilylpropargylic ether: a versatile ambident synthon to access substituted allenyne ethers and alpha-substituted bispropargylic alcohols.
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.
authors.affiliation: CEA-Saclay, iBiTec-S, Service de Chimie Bioorganique et de Marquage, Bât 547, F-91191 Gif sur Yvette cedex, France.
authors.forename: Maude
authors.initials: M
authors.lastname: Brossat
authors.forename: Marie-Pierre
authors.initials: MP
authors.lastname: Heck
authors.forename: Charles
authors.initials: C
authors.lastname: Mioskowski
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D020005:Propanols / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000480:Alkynes; D004987:Ethers; D020005:Propanols; C028255:propargyl alcohol