Enantiomerically pure α-amino acid synthesis via hydroboration -: Suzuki cross-coupling
Enantiomerically pure α-amino acid synthesis via hydroboration -: Suzuki cross-coupling
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DOI：
10.1021/jo010865a
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发表时间：
2002-03-22
影响因子：
3.6
通讯作者：
Taylor, RJK
中科院分区：
文献类型：
--
作者：
Collier, PN;Campbell, AD;Taylor, RJK
加纳醛衍生的亚甲基烯烃 5 和相应的苄氧基羰基化合物 25 与 9-BBN-H 进行硼氢化反应，然后与芳基和乙烯基卤化物进行钯催化的 Suzuki 偶联反应。经过一锅水解-氧化后，一系列已知的和新型的非蛋白氨基酸作为其 N-保护衍生物被分离出来。这些新型有机硼烷高丙氨酸阴离子等价物是在温和条件下生成和转化的，具有广泛的官能团耐受性：富电子和贫电子的芳香族碘化物和溴化物（以及乙烯基溴）均能有效转化。铃木联轴器。还描述了该方法用于制备内消旋 DAP、R,R-DAP 和 R,R-DAS 的扩展。
The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis-oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient. Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described.