Roy Stéphanie, Spino Claude
Département de Chimie, Université de Sherbrooke, Sherbrooke, QC, Canada J1K 2R1.
Org Lett. 2006 Mar 2;8(5):939-42. doi: 10.1021/ol053061g.
Stereocontrolled formation of tertiary or quaternary chiral carbons bearing nitrogen was achieved using the [3,3]-sigmatropic rearrangement of cyanate to isocyanate as a key element. A short and highly selective sequence of reactions, starting from p-menthane-3-carboxaldehyde, was developed leading to alpha,alpha-dialkylated alpha-amino acids or N-heterocycles, depending on the method of cleavage of the auxiliary.
以氰酸酯向异氰酸酯的[3,3] - 迁移重排为关键步骤，实现了含氮叔碳或季碳手性中心的立体控制构建。从对薄荷烷 - 3 - 甲醛出发，开发了一个简短且高选择性的反应序列，根据辅助基团的裂解方法，可得到α,α - 二烷基化α - 氨基酸或N - 杂环化合物。
