Regio- and stereoselective reactions of (S)-(1-methylpyrrolidin-2-yl)methyl allyl sulfide

1991 ◽  
Vol 14 (4) ◽  
pp. 364-369
Author(s):  
Hokoon Park ◽  
Nam Hoon Baik ◽  
Jae Yeol Lee ◽  
Soo Ja Kim ◽  
Won Hoon Ham
2011 ◽  
Author(s):  
J. G. de Vries ◽  
K. Muñiz ◽  
G. Franciò ◽  
W. Leitner ◽  
P. L. Alsters ◽  
...  

ChemInform ◽  
2011 ◽  
Vol 42 (21) ◽  
pp. no-no
Author(s):  
Sten O. Nilsson Lill ◽  
Aaron Forbes ◽  
Patrick Donoghue ◽  
Vincenzo Verdolino ◽  
Olaf Wiest ◽  
...  

ChemInform ◽  
1990 ◽  
Vol 21 (4) ◽  
Author(s):  
A. SOLLADIE-CAVALLO ◽  
S. QUAZZOTTI ◽  
S. COLONNA ◽  
A. MANFREDI

1995 ◽  
Vol 14 (11) ◽  
pp. 5450-5453 ◽  
Author(s):  
Yoshinori Miyauchi ◽  
Saisuke Watanabe ◽  
Hitoshi Kuniyasu ◽  
Hideo Kurosawa

1987 ◽  
Vol 16 (10) ◽  
pp. 1967-1970 ◽  
Author(s):  
Takeshi Takeda ◽  
Shinji Ogawa ◽  
Nagaaki Ohta ◽  
Tooru Fujiwara
Keyword(s):  

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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