Davenport Research Laboratories, Department of Chemistry, University of Toronto, Ontario, Canada.
J Am Chem Soc. 2011 Sep 7;133(35):13770-3. doi: 10.1021/ja205910d. Epub 2011 Aug 10.
A new class of stable molecules, α-boryl aldehydes, has been prepared from oxiranyl N-methyliminodiacetyl boronates by a 1,2-boryl migration with concomitant epoxide scission. A range of boryl imines, alkenes, alcohols, acids, enol ethers, enamides, and other functionalized boronic acid derivatives that are difficult or impossible to prepare using established protocols can be accessed from α-boryl aldehydes. The chemoselective transformations of these building blocks, including the facile synthesis of functionalized unnatural amino acids from silyloxy and amido vinyl boronates, attest to the potential of α-boryl aldehydes in chemical synthesis.
一种新型的稳定分子，α-硼基醛，已经通过环氧基 N-甲基亚氨基二乙酸硼酸盐的 1,2-硼迁移与伴随的环氧化物断裂来制备。一系列硼基亚胺、烯烃、醇、酸、烯醇醚、烯酰胺和其他功能化硼酸衍生物，这些化合物使用已建立的方案难以或不可能制备，都可以从α-硼基醛中获得。这些构建块的化学选择性转化，包括从硅氧基和酰胺基乙烯基硼酸酯中容易地合成功能化的非天然氨基酸，证明了α-硼基醛在化学合成中的潜力。
