Journal of Organic Chemistry p. 8715 - 8724 (2000)
Update date:2022-08-04
Topics: Nitriles Sulfoxides
Dieter
Lu
Velu
α-Aminoalkylcuprates prepared from α-lithio carbamates and CuCN·2LiCl participate in 1,4-addition reactions with α,β-unsaturated esters, thiol esters, imides, and nitriles in poor to excellent yields depending upon the electron-withdrawing substituent and the substitution pattern of the unsaturated substrate. These reagents also undergo conjugate addition reactions with α,β-alkynyl esters, sulfoxides, and nitriles and with α,β-β,γ-unsaturated allenyl esters. Excellent stereocontrol is achieved in the conjugate additions of α-aminoalkylcuprates to the allenyl esters, while poor stereoselectivity results in the conjugate additions to the alkynyl derivatives. Deprotection and cyclization of the alkynyl adducts affords pyrrolin-2-ones, while similar treatment of the allenyl adducts affords 4-alkylidine- pyrrolidin-2-ones and pyrrolizidinones.
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Doi:10.1021/jo990085q
(1999)Doi:10.1039/a607378f
(1997)Doi:10.1016/S0008-6215(00)80059-2
()Doi:10.1016/S0040-4020(99)00129-5
(1999)Doi:10.1002/hlca.19970800315
(1997)Doi:10.1016/S0277-5387(96)00604-3
(1997)