Wen Wei, Ai Zhao-Pin, Yang Chang-Lin, Li Chao-Xing, Wu Zhu-Lian, Cai Tian, Guo Qi-Xiang
Chongqing Key Laboratory of Soft-Matter Material Chemistry and Function Manufacturing, School of Chemistry and Chemical Engineering, Southwest University Chongqing 400715 China
Chem Sci. 2022 Mar 7;13(13):3796-3802. doi: 10.1039/d2sc00386d. eCollection 2022 Mar 30.
Chiral α-amino ketones are common structural motifs in natural products and pharmaceuticals, as well as important synthons in organic synthesis. Thus, establishing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein we disclose a new catalytic asymmetric approach for the synthesis of chiral α-amino ketones through a chiral palladium-catalyzed arylation reaction of generated challenging α-keto imines from previously unreported -acyl -sulfonyl-,-aminals, with arylboronic acids. The current reaction offers a straightforward approach to the asymmetric synthesis of acyclic α-amino ketones in a practical and highly stereocontrolled manner. Meanwhile, the multiple roles of the chiral Pd(ii) complex catalyst in the reaction were also reported.
手性α-氨基酮是天然产物和药物中常见的结构基序，也是有机合成中重要的合成子。因此，建立制备具有这些优势骨架化合物的有效方法是合成化学中的一项重要工作。在此，我们披露了一种新的催化不对称方法，通过手性钯催化从未报道过的α-酰基-磺酰基-α-氨基醛生成具有挑战性的α-酮亚胺与芳基硼酸的芳基化反应来合成手性α-氨基酮。当前反应以实用且高度立体可控的方式为无环α-氨基酮的不对称合成提供了一种直接的方法。同时，还报道了手性Pd(ii)配合物催化剂在反应中的多种作用。
