Organocatalytic Activation of Donor-Acceptor Cyclopropanes: A Tandem (3+3)-Cycloaddition/Aryl Migration toward the Synthesis of Enantioenriched Tetrahydropyridazines

被引：12

作者：

Hazra, Arijit ^{[1
]}

Dey, Raghunath ^{[1
]}

Kushwaha, Apoorv ^{[2
]}

Kumar, T. J. Dhilip ^{[2
]}

Banerjee, Prabal ^{[1
]}

机构：

[1] Indian Inst Technol Ropar, Dept Chem, Lab 406, Rupnagar 140001, Punjab, India

[2] Indian Inst Technol Ropar, Dept Chem, Quantum Dynam Lab, Rupnagar 140001, Punjab, India

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 29期

关键词：

SILYL ETHERS; RACEMIZATION; TRANSFORMATION; REACTIVITY; ALDEHYDES; ACCESS;

D O I：

10.1021/acs.orglett.3c01804

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Anorganocatalytic enantioselective (3 + 3)-cycloaddition reactionof racemic cyclopropane carbaldehydes and aryl hydrazones has beendemonstrated for the first time. A wide range of enantioenriched tetrahydropyridazineswith an exocyclic double bond were obtained with moderate to goodyields and good to excellent enantiomeric excesses. Mechanistic investigationshinted toward a matched/mismatched kinetic resolution, and controlexperiments and DFT calculations unveiled that 1,3-aryl migrationwas concerted and intramolecular and proceeds via a four-memberedtransition state.

引用

页码：5470 / 5475

页数：6

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