unusual rearrangement
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2021 ◽  
Author(s):  
SHYAM SATHYAMOORTHI ◽  
Someshwar Nagamalla ◽  
Joel Mague

We present a new ring-opening reaction of epoxides by pendant silanols, catalyzed by either Ph3C+BF4– or BINOL-phosphoric acid. In all cases examined, the reaction is perfectly regioselective and diastereoselective. Silanol epoxides derived from trans-allylic alcohols, cis-allylic alcohols, trans-homoallylic alcohols, and cis-homoallylic alcohols were all compatible and gave products from either endo- or exo-ring opening. With silanol epoxides derived from 4-alkenyl silanols, an unusual rearrangement to tetrahydrofuran products was observed, which is likely the result of tandem nucleophilic attacks. The utility of this methodology was demonstrated in a short preparation of protected D-arabitol.


Steroids ◽  
2021 ◽  
Vol 172 ◽  
pp. 108853
Author(s):  
Niels Heise ◽  
Bianka Siewert ◽  
Dieter Ströhl ◽  
Sophie Hoenke ◽  
Oxana Kazakova ◽  
...  

2021 ◽  
Author(s):  
Shyam Sathyamoorthi ◽  
Someshwar Nagamalla ◽  
Ranjeet Dhokale ◽  
Frederick Seidl ◽  
Joel Mague

2021 ◽  
Author(s):  
Rui-Li Li ◽  
Qing-Yun Fang ◽  
Mei-Yuan Li ◽  
Xiangshan Wang ◽  
Li-Ming Zhao

An unusual rearrangement of saccharin-derived cyclic ketimines (SDCIs) and 3-chlorooxindoles has been developed to provide a series of spiro-1,3-benzothiazine oxindoles. The reaction features simple manipulation, short reaction time, mild reaction...


Author(s):  
Shyam Sathyamoorthi ◽  
Someshwar Nagamalla ◽  
Frederick Seidl ◽  
Ranjeet Ranjeet Dhokale ◽  
Joel T Mague

We present the first examples of rearrangement reactions of allylic silanol substrates into linear ketone and 5-membered cyclic silanediol organomercurial products. Both reactions are mediated by Hg(OTf)2 but differ in...


2019 ◽  
Author(s):  
Shubham Deolka ◽  
Naziha Tarannam ◽  
robert fayzullin ◽  
sebastian kozuch ◽  
Eugene Khaskin

We report the synthesis of ‘hangman-type’ PNP pincer ligands and their associated Ru complexes. Upon deprotonation, the complexes undergo sp<sup>2</sup>-sp<sup>3</sup> C-C bond cleavage and subsequent C-C formation processes to form a new, one carbon unit longer backbone motif. Unlike the starting geometry, the products are completely inactive in alcohol dehydrogenation catalysis. DFT and mechanistic studies suggest an intramolecular isomerization process via a spyrocycle cyclopropane intermediate, dependent upon arm pyridine coordination and ligand sterics.


2019 ◽  
Author(s):  
Shubham Deolka ◽  
Naziha Tarannam ◽  
robert fayzullin ◽  
sebastian kozuch ◽  
Eugene Khaskin

We report the synthesis of ‘hangman-type’ PNP pincer ligands and their associated Ru complexes. Upon deprotonation, the complexes undergo sp<sup>2</sup>-sp<sup>3</sup> C-C bond cleavage and subsequent C-C formation processes to form a new, one carbon unit longer backbone motif. Unlike the starting geometry, the products are completely inactive in alcohol dehydrogenation catalysis. DFT and mechanistic studies suggest an intramolecular isomerization process via a spyrocycle cyclopropane intermediate, dependent upon arm pyridine coordination and ligand sterics.


2019 ◽  
Vol 55 (76) ◽  
pp. 11350-11353 ◽  
Author(s):  
Shubham Deolka ◽  
Naziha Tarannam ◽  
Robert R. Fayzullin ◽  
Sebastian Kozuch ◽  
Eugene Khaskin

Hangman PNP pincer Ru complexes undergo an unusual sp2–sp3 C–C bond cleavage and formation via a spyrocyclopropane transition state.


2019 ◽  
Vol 48 (9) ◽  
pp. 3052-3060 ◽  
Author(s):  
Alexey Gusev ◽  
Ivan Nemec ◽  
Radovan Herchel ◽  
Victor Shul'gin ◽  
Irina Ryush ◽  
...  

Structure and magnetic data of new Cu(ii) complexes on the bispyridyltriazolylalkanes basis are described.


RSC Advances ◽  
2019 ◽  
Vol 9 (50) ◽  
pp. 29051-29055 ◽  
Author(s):  
Khadija Gambouz ◽  
Mohsine Driowya ◽  
Mohammed Loubidi ◽  
Zahira Tber ◽  
Hassan Allouchi ◽  
...  

A multicomponent reaction giving easy and cheap access to a variety of bicyclic 5,5-fused hetero-rings has been developed.


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