87995-37-7Relevant academic research and scientific papers
Conjugate allylation of cyclic α,β-unsaturated esters
Hofmann, Christine,Baro, Angelika,Laschat, Sabine
scheme or table, p. 1618 - 1622 (2009/04/10)
The conjugate allylation of a homologous series of α,β- unsaturated cyclic esters 8-10 by addition of diallylcuprate (method A), fluoride ion catalyzed addition of trimethylallylsilane (method B), and aluminium tris(2,6-diphenylphenoxide) (ATPH)-mediated addition of allyllithium (method C) was investigated. Method A was not selective in all cases. For methods B and C an influence of ester moiety and ring size on the regioselectivity was observed. Methyl cyclopentenoate 8c gave mainly the 1,2/1,2-product regardless the allylation method while tert-butyl and benzyl ester moieties favored the 1,4-products. For larger rings 9, 10 and the anellated system 19 methods B and C behave complementary depending on the ester function: Method B gave best results of 1,4-addition products for benzyl esters while method C worked better for tert-butyl esters. Thieme Stuttgart.
CHEMOSELECTIVITY IN THE CONJUGATE ADDITION OF ALLYLSILANE TO MICHAEL ACCEPTORS
Majetich, George,Casares, Ada M.,Chapman, D.,Behnke, M.
, p. 1909 - 1912 (2007/10/02)
The allylic carbanion species generated by treatment of allylsilane with fluoride ion undergoes highly chemoselective conjugate addition to a series of Michael acceptors for which alternative known allylation procedures proved less general.
