Issue 51, 2018
From the journal:

Chemical Communications

Diastereoselective addition of anisoles to N-tert-butanesulfinyl imines via four-membered lithium cycles†

Leleti Rajender Reddy, ORCID logo *a   Sharadsrikar Kotturi,a   Yogesh Waman,a   Chirag Patel,a   Aditya Patwaa  and  Rajesh Shenoya  

* Corresponding authors

a Piramal Discovery Solutions, Pharmaceutical Special Economic Zone, Sarkhej Bavla Highway, Ahmedabad, Gujarat 382213, India
E-mail: rajender.leleti@piramal.com

Abstract

A highly regio- and diastereo-selective ortho-lithiation/addition of anisoles to N-tert-butanesulfinyl imines resulting in the selective formation of chiral α-branched amines is described. This method is also efficient for highly regioselective benzylic lithiation of o-methylanisoles, followed by diastereoselective addition to N-tert-butanesulfinyl imines.

Graphical abstract: Diastereoselective addition of anisoles to N-tert-butanesulfinyl imines via four-membered lithium cycles

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Article information

DOI
https://doi.org/10.1039/C8CC03764G
Article type
Communication
Submitted
10 May 2018
Accepted
23 May 2018
First published
24 May 2018

Chem. Commun., 2018,54, 7007-7009

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Diastereoselective addition of anisoles to N-tert-butanesulfinyl imines via four-membered lithium cycles

L. R. Reddy, S. Kotturi, Y. Waman, C. Patel, A. Patwa and R. Shenoy, Chem. Commun., 2018, 54, 7007 DOI: 10.1039/C8CC03764G

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