Copper-catalyzed asymmetric conjugate addition of alkylzirconium reagents to cyclic enones to form quaternary centers

2013 ◽  
Vol 9 (1) ◽  
pp. 104-111 ◽  
Author(s):  
Philippe M C Roth ◽  
Mireia Sidera ◽  
Rebecca M Maksymowicz ◽  
Stephen P Fletcher
Keyword(s):  
Conjugate Addition ◽  
Quaternary Centers ◽  
Cyclic 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

A practical asymmetric conjugate addition to cyclic enones with chiral bifunctional Ru amido catalysts

2012 ◽  
Vol 53 (27) ◽  
pp. 3452-3455 ◽  
Author(s):  
Pavel A. Dub ◽  
Hui Wang ◽  
Masahito Watanabe ◽  
Ilya D. Gridnev ◽  
Takao Ikariya
Keyword(s):  
Conjugate Addition ◽  
Cyclic Enones

ChemInform Abstract: Enantioselective One-Pot Conjugate Addition of Grignard Reagents to Cyclic Enones Followed by Amidomethylation.

ChemInform ◽  
2012 ◽  
Vol 43 (18) ◽  
pp. no-no
Author(s):  
Filip Bilcik ◽  
Michal Drusan ◽  
Jozef Marak ◽  
Radovan Sebesta
Keyword(s):  
Conjugate Addition ◽  
Grignard Reagents ◽  
One Pot ◽  
Cyclic Enones

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.

Enantioselective Copper-Catalyzed Conjugate Addition to Trisubstituted Cyclohexenones: Construction of Stereogenic Quaternary Centers

2005 ◽  
Vol 117 (9) ◽  
pp. 1400-1402 ◽  
Author(s):  
Magali d?Augustin ◽  
La�ticia Palais ◽  
Alexandre Alexakis
Keyword(s):  
Conjugate Addition ◽  
Quaternary Centers
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