School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming, 650500, China.
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, Yunnan University, Kunming, 650091, China.
Org Biomol Chem. 2021 Oct 14;19(39):8607-8612. doi: 10.1039/d1ob01555a.
The chiral keto-substituted propargylamines are an essential class of multifunctional compounds in the field of organic and pharmaceutical synthesis and have attracted considerable attention, but the related synthetic approaches remain limited. Therefore, a concise and efficient method for the enantioselective synthesis of β-keto propargylamines chiral phosphoric acid-catalyzed asymmetric Mannich reaction between β-keto acids and -alkynyl -Boc ,-acetals as easily available -alkynyl imine precursors has been demonstrated here, affording a broad scope of β-keto -Boc-propargylamines in high yields (up to 97%) with generally high enantioselectivities (up to 97 : 3 er).
手性酮取代炔丙胺类化合物是有机和药物合成领域中一类重要的多功能化合物，引起了人们的广泛关注，但相关的合成方法仍然有限。因此，本文展示了一种简洁高效的方法，通过手性磷酸催化β-酮酸与炔丙基 Boc 、-乙酰基 -Boc 作为易得的炔丙基亚胺前体的不对称 Mannich 反应，对β-酮炔丙胺进行对映选择性合成，以高收率（高达 97%）和普遍高对映选择性（高达 97 : 3 er）获得广泛的β-酮 Boc-炔丙胺。
