Department Chemie, Ludwig-Maximilians-University, Butenandtstr. 5-13, Munich, Germany.
J Org Chem. 2011 Nov 4;76(21):8891-906. doi: 10.1021/jo201630e. Epub 2011 Oct 4.
A room-temperature Ni-catalyzed cross-coupling of aryl, heteroaryl, and alkenyl electrophiles with aminoalkylzinc bromides, readily available from the corresponding aminoalkyl chlorides via Grignard reagents, was developed. The reaction allows a convenient one-step preparation of various aminoalkyl products, including piperidine and tropane derivatives. Such functionalized amine moieties are widely present in various biologically active molecules. Aryl, heteroaryl, and alkenyl iodides, bromides, chlorides and triflates are suitable electrophiles. A short total synthesis of two natural products, (±)-galipinine and (±)-cusparine, is also reported.
发展了一种室温下镍催化的芳基、杂芳基和烯基亲电试剂与氨基烷基溴化锌的交叉偶联反应，氨基烷基氯化物可通过格氏试剂很容易地转化为氨基烷基溴化锌。该反应允许方便地一步制备各种氨基烷基产物，包括哌啶和托烷衍生物。这种功能化的胺部分广泛存在于各种生物活性分子中。芳基、杂芳基和烯基碘化物、溴化物、氯化物和三氟甲磺酸酯都是合适的亲电试剂。还报道了两种天然产物(±)-galipinine 和 (±)-cusparine 的简短全合成。
