来自硅烷化α-氨基酸的对映体纯α-氨基醛。
Enantiomerically pure alpha-amino aldehydes from silylated alpha-amino acids.
作者信息
Soto-Cairoli Buddy, de Pomar Jorge Justo, Soderquist John A
机构信息
Department of Chemistry, University of Puerto Rico, Rio Piedras, Puerto Rico 00931-3346.
出版信息
Org Lett. 2008 Jan 17;10(2):333-6. doi: 10.1021/ol7028993. Epub 2007 Dec 20.
Abstract
The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that < or =2% racemization occurs in the 1 --> 8 conversions.
摘要
α-氨基酸1的二硅烷化反应可在不发生消旋化的情况下得到2（产率72 - 87%）。我们设计了一种前所未有的硼烷介导的半还原策略，将2转化为稳定、可分离的恶唑硼烷3（产率100%），3经水解得到纯净、稳定的化合物5（产率49 - 60%）。对γ-氨基酸酯7的Mosher酰胺（8）的分析表明，在1→8的转化过程中发生了≤2%的消旋化。
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