Issue 43, 2017
From the journal:

Organic & Biomolecular Chemistry

An asymmetric acetate-Mannich reaction of chiral isatin derived ketimines and its applications†

Saumen Hajra, ORCID logo *a   Suhas Shivajirao Bhosale ORCID logo ab  and  Atanu Hazra ORCID logo a  

* Corresponding authors

a Centre of Biomedical Research, Sanjay Gandhi Post-Graduate Institute of Medical Sciences Campus, Raebareli Road, Lucknow 226014, India
E-mail: saumen.hajra@cbmr.res.in

b Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India

Abstract

A highly efficient TMSOTf-mediated asymmetric acetate-Mannich reaction of isatin derived tert-butylsulfinyl ketimines and S-phenyl thioacetate was developed to afford the direct synthesis of indole-based β3,3-amino acid thioester with excellent selectivity (dr > 98 : 2). Syntheses of (+)-AG-041R and 3-aminopyrroloindoline have been accomplished utilizing the developed method.

Graphical abstract: An asymmetric acetate-Mannich reaction of chiral isatin derived ketimines and its applications

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C7OB02407J
Article type
Paper
Submitted
27 Sep 2017
Accepted
16 Oct 2017
First published
16 Oct 2017

Org. Biomol. Chem., 2017,15, 9217-9225

Permissions

Request permissions

An asymmetric acetate-Mannich reaction of chiral isatin derived ketimines and its applications

S. Hajra, S. S. Bhosale and A. Hazra, Org. Biomol. Chem., 2017, 15, 9217 DOI: 10.1039/C7OB02407J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements