Institute for Chemical Research, Kyoto University , Uji 611-0011, Japan.
Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University , Kakuma-machi, Kanazawa 920-1192, Japan.
Org Lett. 2017 Jan 20;19(2):352-355. doi: 10.1021/acs.orglett.6b03533. Epub 2017 Jan 3.
A method for asymmetric α-arylation of α-amino acid derivatives via memory of chirality has been developed. Addition of axially chiral enolates, generated from α-amino acid derivatives, to in situ generated arynes, followed by intramolecular C-acylation of the resulting aryl metallic species, gave benzocyclobutenones with a tetrasubstituted carbon with retention of configuration in up to 99% ee.
发展了一种通过手性记忆的方法对α-氨基酸衍生物进行不对称α-芳基化。通过手性轴向烯醇化物，从α-氨基酸衍生物生成，然后与原位生成的芳基炔反应，再进行所得芳基金属物种的分子内 C-酰化反应，得到了四取代碳的苯并环丁烯酮，构型保持在高达 99%的对映体过量。
