Using Stereoelectronic Effects to Explain Selective Reactions of 4-Substituted Five-Membered Ring Oxocarbenium Ions

Deborah M. Smith; K. A. Woerpel

doi:10.1021/ol0492647

Using Stereoelectronic Effects to Explain Selective Reactions of 4-Substituted Five-Membered Ring Oxocarbenium Ions

Organic Letters ◽

10.1021/ol0492647 ◽

2004 ◽

Vol 6 (12) ◽

pp. 2063-2066 ◽

Cited By ~ 34

Author(s):

Deborah M. Smith ◽

K. A. Woerpel

Keyword(s):

Membered Ring ◽

Stereoelectronic Effects ◽

Oxocarbenium Ions

Nucleophilic Addition to Silyl-Protected Five-Membered Ring Oxocarbenium Ions Governed by Stereoelectronic Effects

The Journal of Organic Chemistry ◽

10.1021/jo400945j ◽

2013 ◽

Vol 78 (13) ◽

pp. 6609-6621 ◽

Cited By ~ 15

Author(s):

Vi Tuong Tran ◽

K. A. Woerpel

Keyword(s):

Nucleophilic Addition ◽

Membered Ring ◽

Stereoelectronic Effects ◽

Oxocarbenium Ions

Nucleophilic Additions to Fused Bicyclic Five-Membered Ring Oxocarbenium Ions: Evidence for Preferential Attack on the Inside Face.

ChemInform ◽

10.1002/chin.200411062 ◽

2004 ◽

Vol 35 (11) ◽

Author(s):

Deborah M. Smith ◽

Michelle B. Tran ◽

K. A. Woerpel

Keyword(s):

Membered Ring ◽

Nucleophilic Additions ◽

Oxocarbenium Ions ◽

Inside Face

Stereochemical Reversal of Nucleophilic Substitution Reactions Depending upon Substituent: Reactions of Heteroatom-Substituted Six-Membered-Ring Oxocarbenium Ions through Pseudoaxial Conformers

Journal of the American Chemical Society ◽

10.1021/ja993366o ◽

2000 ◽

Vol 122 (1) ◽

pp. 168-169 ◽

Cited By ~ 138

Author(s):

Jan Antoinette C. Romero ◽

Sarah A. Tabacco ◽

K. A. Woerpel

Keyword(s):

Nucleophilic Substitution ◽

Membered Ring ◽

Substitution Reactions ◽

Nucleophilic Substitution Reactions ◽

Oxocarbenium Ions

Stereoelectronic effects in the hydrolysis of cyclic five-membered-ring phosphate esters. Ab initio and CNDO molecular orbital calculations on alkyloxyphosphoranes

Journal of the American Chemical Society ◽

10.1021/ja00454a053 ◽

1977 ◽

Vol 99 (12) ◽

pp. 4170-4172 ◽

Cited By ~ 35

Author(s):

David G. Gorenstein ◽

Bruce A. Luxon ◽

John B. Findlay ◽

Robert Momii

Keyword(s):

Ab Initio ◽

Molecular Orbital ◽

Membered Ring ◽

Phosphate Esters ◽

Molecular Orbital Calculations ◽

Stereoelectronic Effects ◽

Hydrolysis Of

A Stereoelectronic Model To Explain the Highly Stereoselective Reactions of Nucleophiles with Five-Membered-Ring Oxocarbenium Ions

Journal of the American Chemical Society ◽

10.1021/ja993349z ◽

1999 ◽

Vol 121 (51) ◽

pp. 12208-12209 ◽

Cited By ~ 148

Author(s):

Catharine H. Larsen ◽

Brian H. Ridgway ◽

Jared T. Shaw ◽

K. A. Woerpel

Keyword(s):

Membered Ring ◽

Oxocarbenium Ions ◽

Stereoselective Reactions

Nucleophilic Additions to Fused Bicyclic Five-Membered Ring Oxocarbenium Ions: Evidence for Preferential Attack on the Inside Face

Journal of the American Chemical Society ◽

10.1021/ja0375176 ◽

2003 ◽

Vol 125 (46) ◽

pp. 14149-14152 ◽

Cited By ~ 74

Author(s):

Deborah M. Smith ◽

Michelle B. Tran ◽

K. A. Woerpel

Keyword(s):

Membered Ring ◽

Nucleophilic Additions ◽

Oxocarbenium Ions ◽

Inside Face

StereoselectiveC-Glycosylation Reactions of Ribose Derivatives: Electronic Effects of Five-Membered Ring Oxocarbenium Ions

Journal of the American Chemical Society ◽

10.1021/ja0524043 ◽

2005 ◽

Vol 127 (31) ◽

pp. 10879-10884 ◽

Cited By ~ 140

Author(s):

Catharine H. Larsen ◽

Brian H. Ridgway ◽

Jared T. Shaw ◽

Deborah M. Smith ◽

K. A. Woerpel

Keyword(s):

Membered Ring ◽

Electronic Effects ◽

Oxocarbenium Ions

ChemInform Abstract: STEREOELECTRONIC EFFECTS IN THE HYDROLYSIS OF CYCLIC FIVE-MEMBERED-RING PHOSPHATE ESTERS. AB INITIO AND CNDO MOLECULAR ORBITAL CALCULATIONS ON ALKYLOXYPHOSPHORANES

Chemischer Informationsdienst ◽

10.1002/chin.197736088 ◽

1977 ◽

Vol 8 (36) ◽

pp. no-no

Author(s):

D. G. GORENSTEIN ◽

B. A. LUXON ◽

J. B. FINDLAY ◽

R. MOMII

Keyword(s):

Ab Initio ◽

Molecular Orbital ◽

Membered Ring ◽

Phosphate Esters ◽

Molecular Orbital Calculations ◽

Stereoelectronic Effects ◽

Hydrolysis Of

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

ChemInform ◽

10.1002/chin.200237175 ◽

2010 ◽

Vol 33 (37) ◽

pp. no-no

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

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

The Journal of Organic Chemistry ◽

10.1021/jo010823m ◽

2002 ◽

Vol 67 (7) ◽

pp. 2056-2064 ◽

Cited By ~ 11

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