ethylmagnesium bromide
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Author(s):  
D. Pukazhselvan ◽  
Francisco J. A. Loureiro ◽  
Aliaksandr Shaula ◽  
Sergey Mikhalev ◽  
Igor Bdikin ◽  
...  

Synlett ◽  
2020 ◽  
Vol 31 (05) ◽  
pp. 512-516
Author(s):  
Silvia Gazzola ◽  
Malcolm R. Gordon ◽  
Stephen D. Lindell

Treatment of a solution of a 9-alkyl- or 9-aryl-2-iodopurine in dichloromethane with an ethereal solution of ethylmagnesium bromide at –5 °C generates the corresponding purin-2-ylmagnesium bromide, which reacts with aldehydes to give the corresponding 2-(hydroxyalkyl)purines in yields of 53–84%. The purin-2-yl Grignard reagents show good functional-group tolerance to ester and nitro groups, and the method permits the synthesis of the previously unknown 6-unsubstituted 2-magnesiopurines for the first time. Performing the same procedure in THF as solvent resulted either in extensive decomposition or rapid isomerization to give purin-8-ylmagnesium halides.


Synlett ◽  
2019 ◽  
Vol 30 (03) ◽  
pp. 311-314 ◽  
Author(s):  
Rita Kadikova ◽  
Ilfir Ramazanov ◽  
Oleg Mozgovoi ◽  
Azat Gabdullin ◽  
Usein Dzhemilev

Titanium(IV) isopropoxide and ethylmagnesium bromide catalyzed reaction of 2-alkynylamines with Et2Zn, followed by deuterolysis/hydrolysis and iodinolysis, affords substituted (Z)-pent-2-en-2,5-d 2-1-amines, (Z)-pent-2-en-1-amines (65–88%), and substituted (Z)-2,5-diiodopent-2-en-1-amines (55–63%). It is suggested that the reaction proceeds through the formation of cyclic organotitanium derivatives. The reaction between 1-alkynylphosphines and Et2Zn in the presence of catalytic amounts of Ti(O-iPr)4 and EtMgBr leads to trisubstituted 1-alkenylphosphine oxides with high regioselectivity and stereoselectivity.


Synlett ◽  
2017 ◽  
Vol 29 (04) ◽  
pp. 473-476 ◽  
Author(s):  
Stephen Lindell ◽  
Malcolm Gordon ◽  
Daniel Richards

Treatment of a solution of 9-benzyl or 9-phenyl 6-iodopurine in dichloromethane with an ethereal solution of ethylmagnesium bromide at ambient temperature generates the corresponding purin-6-yl magnesium halides which react with aldehydes to give carbinols in 55–80% yield. Performing the same procedure with THF as solvent gave carbinols in much lower yields (≤15%).


2017 ◽  
Vol 231 ◽  
pp. 379-385 ◽  
Author(s):  
Jae-Hyun Cho ◽  
Jung Hoon Ha ◽  
Sang-Hoon Lee ◽  
Byung Won Cho ◽  
Kyung Yoon Chung ◽  
...  

2015 ◽  
Vol 163 (4) ◽  
pp. H3043-H3051 ◽  
Author(s):  
Lu Chen ◽  
Shufeng Zhao ◽  
Yuping Liu ◽  
Mike Horne ◽  
Alan M. Bond ◽  
...  

Synthesis ◽  
2015 ◽  
Vol 48 (01) ◽  
pp. 136-140 ◽  
Author(s):  
Airat Tuktarov ◽  
Zulfiya Shakirova ◽  
Artur Khuzin ◽  
Usein Dzhemilev

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
K. Chandra Babu ◽  
R. Buchi Reddy ◽  
E. Naresh ◽  
K. Ram Mohan ◽  
G. Madhusudhan ◽  
...  

We report an asymmetric synthesis of (-)-Levetiracetam (1) in six steps starting from versatile new chiralN-sulfinimine (3). The key step, stereoselective 1,2-addition of ethylmagnesium bromide (EtMgBr) to chiralN-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA, gave the corresponding sulfonamide (2) in high diastereoselectivity. Simultaneous deprotection and deacetylation followed by NaIO4cleavage and reduction gaveβ-amino alcohol (6). Subsequent reactions yielded the targeted compound levetiracetam (1).


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