Organic Letters
Organic Letters
5 years ago

Regio- and Stereoselective Anti-Carbozincation of Alkynyl Ethers Using ZnBr2 toward (Z)-β-Zincated Enol Ether Synthesis

Regio- and Stereoselective Anti-Carbozincation of Alkynyl Ethers Using ZnBr2 toward (Z)-β-Zincated Enol Ether Synthesis
Makoto Yasuda, Kyoungmin Kang, Yoshihiro Nishimoto
(Z)-β-Aryloxyalkenylzincs are synthesized stereoselectively via anti-carbozincation among alkynyl ethers, silyl ketene acetals, and ZnBr2. X-ray analysis revealed the structure of the zinc species is a mononuclear two-coordinate dialkenylzinc that is transformed into functionalized enol ethers as a single isomer in the reaction of various electrophiles.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01847

DOI: 10.1021/acs.orglett.7b01847

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