Pyrrole‐Protected β‐Aminoalkylzinc Reagents for the Enantioselective Synthesis of Amino‐Derivatives
作者:Marcel Leroux、Wan‐Yun Huang、Yannick Lemke、Thaddäus J. Koller、Konstantin Karaghiosoff、Paul Knochel
DOI:10.1002/chem.202000870
日期:2020.7.22
prepared starting from optically pure commercial β‐amino‐alcohols. These amino‐alcohols were converted to the corresponding N‐pyrrolyl‐protected alkyl iodides which undergo a zinc insertion in the presence of LiCl (THF, 25 °C, 10–90 min). Subsequent Negishi cross‐coupling or acylation reactions with acid chlorides produced amino‐derivatives with retention of chirality. Diastereoselective CBS‐reductions of
手性 β-氨基烷基卤化锌是从光学纯的商业 β-氨基醇开始制备的。这些氨基醇转化为相应的N-吡咯基保护的烷基碘,在 LiCl 存在下进行锌插入(THF,25 °C,10-90 分钟)。随后的根岸交叉偶联或与酰基氯的酰化反应产生了保留手性的氨基衍生物。一些制备的N-吡咯基酮的非对映选择性 CBS 还原提供了具有高非对映选择性的 1,3-取代的N-吡咯基醇。此外,涉及臭氧分解的脱保护程序可以将吡咯环转化为甲酰胺,而不会损失光学纯度。