Tetrahedron p. 965 - 986 (1993)
Update date:2022-08-06
Topics:
Rossiter, Bryant E.
Eguchi, Masakatsu
Miao, Guobin
Swingle, Nicole M.
Hernandez, Amelia E.
Vickers, Denise
Fluckiger, Ezdan
Greg Patterson
Vasavi Reddy
Scalemic lithium amides derived from primary and secondary amines react with organocopper compounds in ether or dimethyl sulfide to form lithium organo(amido)cuprates capable of enantioselective conjugate addition to 2-cycloalkenones. The most successful heterocuprate, in which the chiral ligand is (S)-N-methyl-1-phenyl-2-(1-piperidinyl)ethanamine, (S)-MAPP, 13, reacts with cyclic enones to form products with up to 97% ee. Nonlinear asymmetric induction was observed with the cuprate formed from ligand 13.
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Doi:10.1016/j.tetlet.2018.05.076
(2018)Doi:10.1016/S0040-4039(00)77500-9
(1993)Doi:10.1039/DT9930000877
(1993)Doi:10.1039/P19930000489
(1993)Doi:10.1021/jacs.5b13337
(2016)Doi:10.1007/BF00944293
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