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Gallium Trihalide Catalyzed Sequential Addition of Two Different Carbon Nucleophiles to Esters by Using Silyl Cyanide and Ketene Silyl Acetals
Author(s) -
Inamoto Yoshihiro,
Kaga Yuta,
Nishimoto Yoshihiro,
Yasuda Makoto,
Baba Akio
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403734
Subject(s) - trihalide , silylation , ketene , nucleophile , chemistry , moiety , catalysis , gallium , organic chemistry , cyanide , carbon fibers , materials science , halide , composite number , composite material
A sequential addition of silyl cyanide and ketene silyl acetals to esters was achieved by a gallium trihalide catalyst to produce β‐cyano‐β‐siloxy esters. This is the first example of the sequential addition of two different carbon nucleophiles to esters. The employment of lactones provided α,α‐disubstituted cyclic ethers with a cyano group and an ester moiety. A variety of esters and lactones are applicable to this reaction system.