@article { ISI:000360510700002, title = {Chiral aziridine ring opening: facile synthesis of (R)-modletine and (R)-phenoxybenzamine hydrochloride}, journal = {Tetrahedron Letters}, volume = {56}, number = {38}, year = {2015}, month = {SEP}, pages = {5269-5271}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A simple and efficient synthesis of chiral drugs (R)-mexiletine 1, an anti-arrhythmic drug and (R)-phenoxybenzamine hydrochloride 2, an anti-hypertensive drug has been described via controlled reductive ring opening of chiral aziridine as a key step. The target compounds 1 and 2 were obtained in overall yields of 34\% and 10.5\%, respectively. (C) 2015 Elsevier Ltd. All rights reserved.

}, keywords = {Aziridine, Mexiletine, Phenoxybenzamine}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2015.07.032}, author = {Viswanadh, N. and Velayudham, R. and Jambu, S. and Sasikumar, M. and Muthukrishnan, Murugan} } @article {48009, title = {cis-aziridine synthon based synthetic investigation for tamiflu employing horner-wadsworth-emmons reaction}, journal = {European Journal of Organic Chemistry}, volume = {2022}, year = {2022}, month = {JUL }, pages = {e202200384}, type = {Article}, abstract = {

Synthetic investigations to achieve a novel intermediate of Tamiflu by using cis-aziridine as a chiral building block, which is readily synthesized from (D)-mannitol as a renewable starting material, has been presented. The present approach utilizes the intramolecular Horner-Wadsworth-Emmons reaction as the key step for the synthesis of Tamiflu. On the other hand, diene containing allylic aziridine framework is found to be inefficient to furnish the six-membered core skeleton of Tamiflu through ring-closing metathesis reaction.

}, keywords = {Aziridine, cyclization, HWE reaction, Metathesis, Tamiflu}, issn = {1434-193X}, doi = {10.1002/ejoc.202200384}, author = {Chavan, Subhash P. and Kawale, Sanket A. and Gonnade, Rajesh G.} } @article {48909, title = {Efficient synthesis of optically active herbicide (S)-metolachlor via reductive ring opening of 2-methoxymethylaziridine}, journal = {Arkivoc}, year = {2023}, month = {JUL}, type = {Article}, abstract = {

An efficient synthesis of a well known chiral herbicide, (S)-metolachlor has been described using 2methoxymethylaziridine ring formation and reductive ring opening as key steps using commercially available (R)-epichlorohydrin. The present protocol delivers the required enantiomer of metolachlor in overall yield of 50.8\% and high enantiopurity (\>99\%).

}, keywords = {Aziridine, Epoxide, Epoxide ring opening, herbicide synthesis, Metolachlor}, issn = {1551-7004}, doi = {10.24820/ark.5550190.p011.954}, author = {Nalla, Viswanadh and Mujahid, Mohammad and Sasikumar, Murugesan and Mujumdar, Prashant and Muthukrishnan, Murugan} }