ChemInform Abstract: Effect of Conformational Rigidity on the Stereoselectivity of Nucleophilic Additions to Five-Membered Ring Bicyclic Oxocarbenium Ion Intermediates.

ChemInform ◽  
2015 ◽  
Vol 46 (7) ◽  
pp. no-no
Author(s):  
Olga Lavinda ◽  
Vi Tuong Tran ◽  
K. A. Woerpel
Keyword(s):  
Membered Ring ◽  
Nucleophilic Additions ◽  
Conformational Rigidity ◽  
Oxocarbenium Ion

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.

scholarly journals Stereoelectronic Model To Explain Highly Stereoselective Reactions of Seven-Membered-Ring Oxocarbenium-Ion Intermediates

2016 ◽  
Vol 128 (5) ◽  
pp. 1848-1851 ◽  
Author(s):  
Matthew G. Beaver ◽  
Trixia M. Buscagan ◽  
Olga Lavinda ◽  
K. A. Woerpel
Keyword(s):  
Membered Ring ◽  
Oxocarbenium Ion ◽  
Stereoselective Reactions

scholarly journals Stereoelectronic Model To Explain Highly Stereoselective Reactions of Seven-Membered-Ring Oxocarbenium-Ion Intermediates

2016 ◽  
Vol 55 (5) ◽  
pp. 1816-1819 ◽  
Author(s):  
Matthew G. Beaver ◽  
Trixia M. Buscagan ◽  
Olga Lavinda ◽  
K. A. Woerpel
Keyword(s):  
Membered Ring ◽  
Oxocarbenium Ion ◽  
Stereoselective Reactions

An Alternate Energy-Conserved Pathway for the Morita-Baylis-Hillman (MBH) Reaction

2020 ◽  
Author(s):  
Veejendra Yadav
Keyword(s):  
Proton Transfer ◽  
Transition State ◽  
Lower Energy ◽  
Aldol Reaction ◽  
Membered Ring ◽  
Ammonium Ion ◽  
Alternate Energy ◽  
Ring Transition State ◽  
Mbh Reaction

An new overall lower energy pathway for the amine-catalysed Morita-Baylis-Hillman reaction is proposed from computations at the M06-2X/6-311++G(d,p) level. The pathway involves proton-transfer from the ammonium ion to the alkoxide formed from the aldol reaction through a seven-membered ring transition state (TS) structure followed by highly exothermic Hofmann<i> </i>elimination through a five-membered ring TS structure to form the product and also release the catalyst to carry on with the process all over again.

An Alternate Energy-Conserved Pathway for the Morita-Baylis-Hillman (MBH) Reaction

2020 ◽  
Author(s):  
Veejendra Yadav
Keyword(s):  
Proton Transfer ◽  
Transition State ◽  
Lower Energy ◽  
Aldol Reaction ◽  
Membered Ring ◽  
Ammonium Ion ◽  
Alternate Energy ◽  
Ring Transition State ◽  
Mbh Reaction

An new overall lower energy pathway for the amine-catalysed Morita-Baylis-Hillman reaction is proposed from computations at the M06-2X/6-311++G(d,p) level. The pathway involves proton-transfer from the ammonium ion to the alkoxide formed from the aldol reaction through a seven-membered ring transition state (TS) structure followed by highly exothermic Hofmann<i> </i>elimination through a five-membered ring TS structure to form the product and also release the catalyst to carry on with the process all over again.

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