Significance of the anomeric effect on the configurational stability of cyclopropyl carbanions

1986 ◽  
Vol 27 (23) ◽  
pp. 2555-2558 ◽  
Author(s):  
Albert Padwa ◽  
M.Woods Wannamaker
ChemInform ◽  
2010 ◽  
Vol 22 (5) ◽  
pp. no-no
Author(s):  
E. JAUDAS-PREZEL ◽  
R. MAGGIULLI ◽  
R. MEWS ◽  
H. OBERHAMMER ◽  
T. PAUST ◽  
...  
Keyword(s):  

RSC Advances ◽  
2015 ◽  
Vol 5 (45) ◽  
pp. 35412-35420 ◽  
Author(s):  
Thaís M. Barbosa ◽  
Renan V. Viesser ◽  
Raymond J. Abraham ◽  
Roberto Rittner ◽  
Cláudio F. Tormena

Which analysis will explain the preferences of the substituents in the hydro-halo-tetrahydropyran rings? Is the anomeric effect essential to understand what is going on?


1989 ◽  
Vol 10 (2) ◽  
pp. 265-283 ◽  
Author(s):  
Pinchas Aped ◽  
Leah Schleifer ◽  
Benzion Fuchs ◽  
Saul Wolfe
Keyword(s):  

1997 ◽  
Vol 36 (24) ◽  
pp. 2784-2786 ◽  
Author(s):  
Dieter Hoppe ◽  
Bernd Kaiser ◽  
Oliver Stratmann ◽  
Roland Fröhlich

1978 ◽  
Vol 9 (6) ◽  
Author(s):  
B. S. JENSEN ◽  
R. LINES ◽  
P. PAGSBERG ◽  
V. D. PARKER

2021 ◽  
Author(s):  
Eric Miller ◽  
Maciej Walczak

Stereoselective reactions at the anomeric carbon constitute the cornerstone of preparative carbohydrate chemistry. Here, we report the synthesis of axial C1 trifluoroborates and stereoselective C-arylation and etherification reactions under photoredox conditions. These reactions are characterized by high anomeric selectivities for 2-deoxysugars and broad substrate scope (24 examples), including disaccharides and trifluoroborates with free hydroxyl groups. Computational studies show that high axial selectivities for these reactions originate from a combination of kinetic anomeric effect of the intermediate C1 radical and stereoelectronic stabilization of Ni(III) through the metallo-anomeric effect. Taken together, this new class of carbohydrate reagents adds the palette of anomeric nucleophile reagents suitable for efficient installation C-C and Cheteroatom bonds.


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