Diastereoselective Spirocyclization via Intramolecular C(sp3)-H Bond Functionalization Triggered by Sequential [1,5]-Hydride Shift/Cyclization Process: Approach to Spiro-tetrahydroquinolines

被引：10
作者：
Bhowmik, Arup [1 ]
Das, Sumit [1 ,2 ]
Sarkar, Writhabrata [1 ]
Saidalavi, K. M. [1 ]
Mishra, Aniket [1 ]
Roy, Anupama [1 ]
Deb, Indubhusan [1 ]
机构：
[1] Indian Inst Chem Biol, Organ & Med Chem Div, 4 Raja SC Mullick Rd, Kolkata 700032, India
[2] Acad Sci & Innovat Res AcSIR, Kamla Nehru Nagar 201002, Ghaziabad, India
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2021年 / 363卷 / 03期
关键词：
1,5]-hydride shift reaction; Lewis acid catalyst; Spirocycles; tetrahydroisoquinoline; 2-coumaranone; 3-isochromanone; C-H BOND; RING-CLOSURE REACTIONS; HYDRIDE TRANSFER; ASYMMETRIC-SYNTHESIS; HETEROCYCLIC SYNTHESIS; CATALYZED DIRECT; TOPOISOMERASE-I; CASCADE; CONSTRUCTION; TANDEM;
D O I：
10.1002/adsc.202001011
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A direct synthesis of spiro[5.5]and [5.4]-tetrahydroquinolines has been developed through C(sp(3))-H bond functionalization triggered by sequential [1,5]- hydride shift /cyclization sequence using ortho amino benzaldehydes and active methylene compounds such as 2-coumaranone, 4-hydroxycoumarin, 3-coumaranone, and 3-isochromanone. This protocol provides a Lewis acid catalyst-free straight forward one-pot reaction in cases of 2-coumaranone and 4-hydroxycoumarin, Lewis acid-catalyzed stepwise reaction for 3-coumaranone and 3-isochromanone to access a wide range of spiro-heterocycles in excellent to good yields and diastereoselectivity.
引用
收藏
页码：826 / 832
页数：7
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