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

Deborah M. Smith; Michelle B. Tran; K. A. Woerpel

doi:10.1021/ja0375176

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

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

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

ChemInform ◽

10.1002/chin.201507024 ◽

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

Nucleophilic Additions of Trimethylsilyl Cyanide to Cyclic Oxocarbenium Ions: Evidence for the Loss of Stereoselectivity at the Limits of Diffusion Control

Journal of the American Chemical Society ◽

10.1021/ja061110u ◽

2006 ◽

Vol 128 (26) ◽

pp. 8671-8677 ◽

Cited By ~ 37

Author(s):

Siddhartha R. Shenoy ◽

Deborah M. Smith ◽

K. A. Woerpel

Keyword(s):

Diffusion Control ◽

Nucleophilic Additions ◽

Trimethylsilyl Cyanide ◽

Oxocarbenium Ions

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

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

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

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: 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

ChemInform Abstract: CYCLOPENTADIENONE COMPLEXES AS FIVE-MEMBERED-RING SYNTHONS: RING- AND REGIOSPECIFIC NUCLEOPHILIC ADDITIONS TO COBALTOCENIUM SALTS AND ELABORATION TO SUBSTITUTED CYCLOPENTADIENES AND CYCLOPENTENONES

Chemischer Informationsdienst ◽

10.1002/chin.198244297 ◽

1982 ◽

Vol 13 (44) ◽

Author(s):

J. P. TANE ◽

K. P. C. VOLLHARDT

Keyword(s):

Membered Ring ◽

Nucleophilic Additions

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

Organic & Biomolecular Chemistry ◽

10.1039/c4ob01251h ◽

2014 ◽

Vol 12 (36) ◽

pp. 7083-7091 ◽

Cited By ~ 14

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.