Options
One-Pot Regio- and Diastereoselective Synthesis of Tetrahydro-α-carbolines via Cascade Reactions of Iminoindolines with Morita-Baylis-Hillman Bromides of Nitroalkenes
Journal
European Journal of Organic Chemistry
ISSN
1434193X
Date Issued
2022-01-21
Author(s)
Sivanandan, Sudheesh T.
Chauhan, Diksha
Namboothiri, Irishi N.N.
Abstract
A mild and metal-free method for the one-pot synthesis of highly substituted tetrahydro-α-carbolines from Morita-Baylis-Hillman (MBH) bromides of nitroalkenes and iminoindolines has been demonstrated. Cascade reaction of MBH bromides with tosyliminoindolines occurs with regio- as well as diastereoselectivity in a formal [3+3] manner to form various tetrahydro-α-carbolines with wide substrate scope under mild conditions. All the products were obtained in high yields within a short reaction time. Also, the synthetic efficiency of the methodology was demonstrated by a gram scale experiment and by further converting them into 3-nitro-α-carbolines.