Asymmetric tandem conjugate addition–protonation to forge chiral secondary C–O bonds for quaternary carbon stereocenters at the nonadjacent β-position

2017 ◽  
Vol 53 (54) ◽  
pp. 7493-7496 ◽  
Author(s):  
San-Ni Hong ◽  
Yang Liu ◽  
Richmond Lee ◽  
Zhiyong Jiang
Keyword(s):  
Conjugate Addition ◽  
Quaternary Carbon ◽  
Efficient Approach

The first asymmetric tandem conjugate addition–protonation to methylene 1,3-oxazolidine-2,4-diones has been developed, thus providing a direct and efficient approach to assemble chiral secondary C–O bonds for quaternary carbon stereocenters and thiols at the nonadjacent β-position.

scholarly journals Desymmetrization of cyclic 1,3-diketones via Ir-catalyzed hydrogenation: an efficient approach to cyclic hydroxy ketones with a chiral quaternary carbon

2019 ◽  
Vol 10 (25) ◽  
pp. 6350-6353 ◽  
Author(s):  
Quan Gong ◽  
Jialin Wen ◽  
Xumu Zhang
Keyword(s):  
Efficient Method ◽  
Quaternary Carbon ◽  
Efficient Approach ◽  
Quaternary Center ◽  
Hydroxy Ketones

We herein report an efficient method to synthesize cyclic hydroxy ketones with a chiral quaternary center.

Stereoselective formation of tertiary and quaternary carbon centers via inverse conjugate addition of carbonucleophiles to allenic esters

Tetrahedron ◽  
2010 ◽  
Vol 66 (39) ◽  
pp. 7720-7725 ◽  
Author(s):  
Ana Lúcia Cardoso ◽  
Ana Matos Beja ◽  
Manuela Ramos Silva ◽  
Jesús M. de los Santos ◽  
Francisco Palacios ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Quaternary Carbon ◽  
Carbon Centers ◽  
Allenic Esters

ChemInform Abstract: Trends in Organocatalytic Conjugate Addition to Enones: An Efficient Approach to Optically Active Alkynyl, Alkenyl, and Ketone Products.

ChemInform ◽  
2010 ◽  
Vol 41 (3) ◽  
Author(s):  
Marcio Weber Paixao ◽  
Nicole Holub ◽  
Carlos Vila ◽  
Martin Nielsen ◽  
Karl Anker Joergensen
Keyword(s):  
Conjugate Addition ◽  
Optically Active ◽  
Efficient Approach

Trends in Organocatalytic Conjugate Addition to Enones: An Efficient Approach to Optically Active Alkynyl, Alkenyl, and Ketone Products

2009 ◽  
Vol 48 (40) ◽  
pp. 7338-7342 ◽  
Author(s):  
Márcio Weber Paixão ◽  
Nicole Holub ◽  
Carlos Vila ◽  
Martin Nielsen ◽  
Karl Anker Jørgensen
Keyword(s):  
Conjugate Addition ◽  
Optically Active ◽  
Efficient Approach

scholarly journals A versatile and efficient approach for the synthesis of chiral 1,3-nitroamines and 1,3-diamines via conjugate addition to new (S,E)-γ-aminated nitroalkenes derived from L-α-amino acids

2013 ◽  
Vol 9 ◽  
pp. 832-837 ◽  
Author(s):  
Vera Lúcia Patrocinio Pereira ◽  
André Luiz da Silva Moura ◽  
Daniel Pais Pires Vieira ◽  
Leandro Lara de Carvalho ◽  
Eliz Regina Bueno Torres ◽  
...  
Keyword(s):  
Amino Acids ◽  
Direct Reduction ◽  
Conjugate Addition ◽  
The Other ◽  
Triazole Derivative ◽  
Cyanide Anion ◽  
Efficient Approach ◽  
Azide Anion ◽  
Other Hand

New chiral (S,E)-γ-N,N-dibenzylated nitroalkenes 2a–c were synthesized from natural L-(α)-amino acids in five steps with overall yields of 68–88%. The conjugate addition of hydride, methoxide, nitronate and azide nucleophiles to 2a–c led to the corresponding chiral 1,3-nitroamines in 74–90% yield. The conjugate addition of cyanide anion to 2a,b was followed by HNO2 elimination affording chiral aminated acrylonitriles (73–98%). On the other hand, the azide anion reacted with 2a, in acetonitrile, via a [3 + 2]-cycloaddition in which HNO2 was lost, providing the corresponding 1,2,3-triazole derivative. Direct reduction of 1,3-nitroamine derivatives 9a,b produced the corresponding 1,3-diamines in good yields.

Enantioselective Copper-Catalyzed Conjugate Addition to 2- or 3-Substituted Cyclopent-2-en-1-ones: Construction of Stereogenic Quaternary Carbon Centers

Synlett ◽  
2007 ◽  
Vol 2007 (13) ◽  
pp. 2057-2060 ◽  
Author(s):  
Alexandre Alexakis ◽  
Magali Vuagnoux-d’Augustin ◽  
Stefan Kehrli
Keyword(s):  
Conjugate Addition ◽  
Quaternary Carbon ◽  
Carbon Centers
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