Diastereoselective Nucleophilic Substitution Reactions of Oxasilacyclopentane Acetals:  Application of the “Inside Attack” Model for Reactions of Five-Membered Ring Oxocarbenium Ions

2002 ◽  
Vol 67 (7) ◽  
pp. 2056-2064 ◽  
Author(s):  
Teresa J. Bear ◽  
Jared T. Shaw ◽  
K. A. Woerpel
Keyword(s):  
Nucleophilic Substitution ◽  
Membered Ring ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions ◽  
Attack Model ◽  
Oxocarbenium Ions

scholarly journals Effect of conformational rigidity on the stereoselectivity of nucleophilic additions to five-membered ring bicyclic oxocarbenium ion intermediates

2014 ◽  
Vol 12 (36) ◽  
pp. 7083-7091 ◽  
Author(s):  
Olga Lavinda ◽  
Vi Tuong Tran ◽  
K. A. Woerpel
Keyword(s):  
Nucleophilic Substitution ◽  
Membered Ring ◽  
Nucleophilic Additions ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions ◽  
Conformational Rigidity ◽  
Fused Ring ◽  
Oxocarbenium Ion

Nucleophilic substitution reactions of five-membered ring acetals bearing fused rings reveal that subtle changes in the structure of the fused ring can exert dramatic influences on selectivity.

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