Azomethine ylide cycloaddition of 1,3-dienyl esters: highly regio- and diastereoselective synthesis of functionalized pyrrolidinochromenes

Bakthadoss, Manickam and Mushaf, Mohammad and Agarwal, Vishal and Reddy, Tadiparthi Thirupathi and Sharada, D S (2022) Azomethine ylide cycloaddition of 1,3-dienyl esters: highly regio- and diastereoselective synthesis of functionalized pyrrolidinochromenes. Organic & Biomolecular Chemistry, 20 (4). pp. 778-782. ISSN 1477-0520

Text
Organic_and_Biomolecular_Chemistry.pdf - Published Version
Restricted to Registered users only
Download (1MB) | Request a copy

Abstract

An efficient protocol for the synthesis of tricyclic pyrrolidinochromenes has been developed via an intramolecular 1,3-dipolar cycloaddition of azomethine ylides generated in situ from 1,3-dienyl ester tethered O-hydroxyarylaldehyde and glycine esters. The reaction is highly regio- and diastereoselective in nature and provided the potentially bioactive pyrrolidine fused tricyclic cycloadducts in excellent yields with wide substrate scope. Interestingly this reaction constructs two rings and four contiguous stereogenic centers in which one of them is an all carbon quaternary center in a unique fashion. This journal is © The Royal Society of Chemistry.

[error in script]

IITH Creators:

IITH Creators	ORCiD
Sharada, D S	UNSPECIFIED

Item Type:

Article

Additional Information:

The authors thank DST-SERB (ref no.: CRG/2019/006323) for financial support. V. A. and T. T. R. thank CSIR, New Delhi for Direct-Senior Research Fellowship (D-SRF). We also acknowledge the Central Instrumentation Facility (CIF), Pondicherry University for NMR spectra, and DST-FIST for the ESI-HRMS facility.

Uncontrolled Keywords:

3-dipolar cycloaddition; Azomethine ylides; Bioactives; Cycloadditions; Diastereoselective; Diastereoselective synthesis; Efficient protocols; Functionalized; Regio-selective; Regioselective synthesis

Subjects:

Chemistry

Divisions:

Department of Chemistry

Depositing User:

. LibTrainee 2021

Date Deposited:

14 Jul 2022 10:47

Last Modified:

14 Jul 2022 10:47

URI:

http://raiithold.iith.ac.in/id/eprint/9698