Enantioselective conjugate addition of 3-fluoro-oxindoles to vinyl sulfone: an organocatalytic access to chiral 3-fluoro-3-substituted oxindoles

2013 ◽  
Vol 11 (32) ◽  
pp. 5217 ◽  
Author(s):  
Xiaowei Dou ◽  
Yixin Lu
Keyword(s):  
Conjugate Addition ◽  
Vinyl Sulfone

Conjugate addition of moderately soft anions to a vinyl sulfone

1983 ◽  
Vol 48 (6) ◽  
pp. 914-916 ◽  
Author(s):  
P. R. Hamann ◽  
P. L. Fuchs
Keyword(s):  
Conjugate Addition ◽  
Vinyl Sulfone

Highly Enantioselective Conjugate Addition of 3-Substituted Oxindoles to Vinyl Sulfone Catalyzed by Binaphthyl-Modified Tertiary Amines

Synlett ◽  
2011 ◽  
Vol 2011 (11) ◽  
pp. 1559-1562 ◽  
Author(s):  
Dae Kim ◽  
Hyun Lee ◽  
Seung Kang
Keyword(s):  
Conjugate Addition ◽  
Vinyl Sulfone ◽  
Tertiary Amines

Enantioselective Conjugate Addition of Nitroalkanes to Vinyl Sulfone: An Organocatalytic Access to Chiral Amines

2009 ◽  
Vol 11 (8) ◽  
pp. 1721-1724 ◽  
Author(s):  
Qiang Zhu ◽  
Yixin Lu
Keyword(s):  
Conjugate Addition ◽  
Chiral Amines ◽  
Vinyl Sulfone

ChemInform Abstract: CONJUGATE ADDITION OF MODERATELY SOFT ANIONS TO A VINYL SULFONE

1983 ◽  
Vol 14 (33) ◽  
Author(s):  
P. R. HAMANN ◽  
P. L. FUCHS
Keyword(s):  
Conjugate Addition ◽  
Vinyl Sulfone

Nucleic acid related compounds. 67. Synthesis of 5′-amino and 5′-methylthio chain-extended nucleosides from uridine

1991 ◽  
Vol 69 (12) ◽  
pp. 2104-2111 ◽  
Author(s):  
Stanislaw F. Wnuk ◽  
N. Kent Dalley ◽  
Morris J. Robins
Keyword(s):  
Nucleic Acid ◽  
Sodium Borohydride ◽  
Conjugate Addition ◽  
Amino Derivative ◽  
Vinyl Sulfone ◽  
X Ray ◽  
Basic Solutions ◽  
High Yields ◽  
Wittig Reagent ◽  
Related Compounds

Treatment of 2′,3′-O-isopropylideneuridine-5′-aldehyde with the stabilized Wittig reagent, (p-toluenesulfonylmethylene)triphenylphosphorane, gave high yields of 1-[5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-ribo-hex-5(E)-enofuranosyl]uracil (2). This vinylsulfone (2) underwent isomerization readily in base to give the allylic sulfone, 1-[5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-erythro-hex-4(Z)-enofuranosyl]uracil (3). Treatment of 2 or 3 with aqueous trifluoroacetic acid gave the corresponding deprotected vinyl (5) or allylic (6) sulfones, and 5 was converted to 6 readily in basic solutions. Treatment of 2 with sodium borohydride, sodium thiomethoxide, or ammonia resulted in conjugate addition (at C5′ of the vinyl sulfone) to give the 5′-hydro, 5′-methylthio, or 5′-amino-5′,6′-dideoxy-6′-(p-toluenesulfonyl) nucleosides. The 5′-substituted diastereomers were deprotected, separated, and the configuration of a 5′-amino derivative was established by X-ray crystallography.Key words: allylic sulfones, amino-nucleosides, 5′,6′-dideoxynucleosides, nucleosides, uridine, vinyl sulfones.

ChemInform Abstract: Highly Enantioselective Conjugate Addition of 3-Substituted Oxindoles to Vinyl Sulfone Catalyzed by Binaphthyl-Modified Tertiary Amines.

ChemInform ◽  
2011 ◽  
Vol 42 (47) ◽  
pp. no-no
Author(s):  
Hyun Joo Lee ◽  
Seung Hee Kang ◽  
Dae Young Kim
Keyword(s):  
Conjugate Addition ◽  
Vinyl Sulfone ◽  
Tertiary Amines

ChemInform Abstract: Organocatalytic Enantioselective Conjugate Addition of 3-Fluorooxindoles to Vinyl Sulfone.

ChemInform ◽  
2015 ◽  
Vol 46 (40) ◽  
pp. no-no
Author(s):  
Yi Seul Kim ◽  
Su Jin Kwon ◽  
Dae Young Kim
Keyword(s):  
Conjugate Addition ◽  
Vinyl Sulfone
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