Remote Construction of Chiral Vicinal Tertiary and Quaternary Centers by Catalytic Asymmetric 1,6-Conjugate Addition of Prochiral Carbon Nucleophiles to Cyclic Dienones

2015 ◽  
Vol 21 (52) ◽  
pp. 18921-18924 ◽  
Author(s):  
Yuan Wei ◽  
Zunwu Liu ◽  
Xinxin Wu ◽  
Jie Fei ◽  
Xiaodong Gu ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Quaternary Centers ◽  
Carbon Nucleophiles ◽  
Catalytic Asymmetric

scholarly journals Acyclic quaternary centers from asymmetric conjugate addition of alkylzirconium reagents to linear trisubstituted enones

2017 ◽  
Vol 8 (1) ◽  
pp. 641-646 ◽  
Author(s):  
Zhenbo Gao ◽  
Stephen P. Fletcher
Keyword(s):  
Conjugate Addition ◽  
Synthetic Methods ◽  
Quaternary Centers ◽  
Cyclic Systems ◽  
Catalytic Asymmetric ◽  
Selective Formation

Synthetic methods for the selective formation of all carbon quaternary centres in non-cyclic systems are rare. Here we report highly enantioselective Cu-catalytic asymmetric conjugate addition of alkylzirconium species to twelve different acyclic trisubstituted enones.

scholarly journals Formation of Quaternary Centers by Copper-Catalyzed Asymmetric Conjugate Addition of Alkylzirconium Reagents

2013 ◽  
Vol 125 (31) ◽  
pp. 8153-8157 ◽  
Author(s):  
Mireia Sidera ◽  
Philippe M. C. Roth ◽  
Rebecca M. Maksymowicz ◽  
Stephen P. Fletcher
Keyword(s):  
Conjugate Addition ◽  
Quaternary Centers

ChemInform Abstract: Direct Catalytic Asymmetric Conjugate Addition of Saturated and Unsaturated Thioamides.

ChemInform ◽  
2015 ◽  
Vol 46 (45) ◽  
pp. no-no
Author(s):  
Nilanjana Majumdar ◽  
Akira Saito ◽  
Liang Yin ◽  
Naoya Kumagai ◽  
Masakatsu Shibasaki
Keyword(s):  
Conjugate Addition ◽  
Catalytic Asymmetric

Enantioselective Construction of Alkylated Centers: The Maier Synthesis of Platencin

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Conjugate Addition ◽  
Unsaturated Ketone ◽  
West Virginia University ◽  
Aryl Iodide ◽  
Quaternary Centers ◽  
University Of New Mexico ◽  
Conjugate Reduction ◽  
Complementary Approach ◽  
Stereogenic Centers ◽  
The University

Jaesook Yun of Sungkyunkwan University devised (J. Org. Chem. 2009, 74, 4232) a method, based on conjugate addition to a cyano alkyne, for the preparation of nitriles such as 1 with high geometric control. Enantioselective conjugate reduction then delivered the doubly arylated stereogenic center of 2 in high ee. Pher G. Andersson of Uppsala University described (J. Am. Chem. Soc. 2009, 131, 8855) a similar approach to diarylated ternary stereogenic centers. Motomu Kanai and Masakatsu Shibasaki of the University of Tokyo developed (J. Am. Chem. Soc. 2009, 131, 3858) a complementary approach to dialkylated stereogenic centers based on enantioselective conjugate cyanation of α-methylene N-acylpyrroles such as 3. Cathleen M. Crudden of Queen’s University established (J. Am. Chem. Soc. 2009, 131, 5024) that a benzylic organoborane, prepared by enantioselective hydroboration of styrene, coupled with an aryl iodide such as 6 in good yield and with > 90% retention of ee. Kwunmin Chen of National Taiwan Normal University devised ( Adv. Synth. Cat. 2009, 351, 1273) an organocatalyst for the enantioselective Michael addition of an α,α,-dialkyl aldehyde such as 9 to a nitroalkene. Wenhu Duan of the East China University of Science and Technology and Wei Wang of the University of New Mexico together developed (Organic Lett. 2009, 11, 2864) an organocatalyst for the enantioselective addition of nitromethane 12 to an unsaturated ketone such as 11. Xiaodong Shi of West Virginia University found (Angew. Chem. Int. Ed. 2009, 48, 1279) that commercial diphenyl prolinol effectively promoted enantioselective conjugate addition of 15 to 14. Enantioselective methods for the construction of alkylated quaternary centers have also been put forward. Kin-ichi Tadano of Keio University devised (Tetrahedron Lett. 2009, 50, 1139) a glucose-derived chiral auxiliary that effectively directed the absolute sense of the alkylation of 17. Li Deng of Brandeis University reported (Tetrahedron 2009, 65, 3139) further details of his elegant Cinchona -mediated conjugate addition of 19 to 20. Francesca Marini of the Università degli Studi di Perugia extended (Adv. Synth. Cat. 2009, 351, 103) this approach to selenones, effecting, over two steps, enantioselective vinylation.

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