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

页码：826 / 832

页数：7

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