Electrocremical procedure directed to the selective ring opening of epoxides to allylic alcohols

1984 ◽  
Vol 25 (37) ◽  
pp. 4137-4138 ◽  
Author(s):  
Kenji Uneyama ◽  
Noriyuki Nisiyama ◽  
Sigeru Torii
Keyword(s):  
Ring Opening ◽  
Allylic Alcohols ◽  
Selective Ring Opening ◽  
Ring Opening Of Epoxides

Regio- and stereo-selective ring opening of epoxides with amide cuprate reagents

1993 ◽  
pp. 1201 ◽  
Author(s):  
Yoshinori Yamamoto ◽  
Naoki Asao ◽  
Masaki Meguro ◽  
Naofumi Tsukada ◽  
Hisao Nemoto ◽  
...  
Keyword(s):  
Ring Opening ◽  
Selective Ring Opening ◽  
Ring Opening Of Epoxides

Studies towards the Taming of the ‘Carbocation’ in the Regioselective Ring Opening of Epoxides to Allylic Alcohols

Synlett ◽  
2010 ◽  
Vol 2010 (04) ◽  
pp. 595-598 ◽  
Author(s):  
William Motherwell ◽  
Helen Chapman ◽  
Karim Herbal
Keyword(s):  
Ring Opening ◽  
Allylic Alcohols ◽  
Ring Opening Of Epoxides

scholarly journals Ring-Opening of Epoxides by Pendant Silanols

2021 ◽  
Author(s):  
SHYAM SATHYAMOORTHI ◽  
Someshwar Nagamalla ◽  
Joel Mague
Keyword(s):  
Phosphoric Acid ◽  
Ring Opening ◽  
Allylic Alcohols ◽  
Homoallylic Alcohols ◽  
Unusual Rearrangement ◽  
Ring Opening Reaction ◽  
Ring Opening Of Epoxides

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.

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