Catalytic Enantioselective Conjugate Reduction ofβ,β-Disubstituted Nitroalkenes

2003 ◽  
Vol 42 (39) ◽  
pp. 4793-4795 ◽  
Author(s):  
Constantin Czekelius ◽  
Erick M. Carreira
Keyword(s):  
Conjugate Reduction

ChemInform Abstract: Asymmetric Conjugate Reduction of α,β-Unsaturated Esters Using a Chiral Phosphine-Copper Catalyst.

ChemInform ◽  
2010 ◽  
Vol 31 (4) ◽  
pp. no-no
Author(s):  
Daniel H. Appella ◽  
Yasunori Moritani ◽  
Ryo Shintani ◽  
Eric M. Ferreira ◽  
Stephen L. Buchwald
Keyword(s):  
Copper Catalyst ◽  
Unsaturated Esters ◽  
Conjugate Reduction

Catalytic Enantioselective Conjugate Reduction of β,β-Disubstituted Nitroalkenes.

ChemInform ◽  
2004 ◽  
Vol 35 (6) ◽  
Author(s):  
Constantin Czekelius ◽  
Erick M. Carreira
Keyword(s):  
Conjugate Reduction

Asymmetric Conjugate Reduction of α,β-Unsaturated Ketones and Esters with Chiral Rhodium(2,6-bisoxazolinylphenyl) Catalysts.

ChemInform ◽  
2006 ◽  
Vol 37 (19) ◽  
Author(s):  
Yoshinori Kanazawa ◽  
Yasunori Tsuchiya ◽  
Kazuki Kobayashi ◽  
Takushi Shiomi ◽  
Jun-ichi Itoh ◽  
...  
Keyword(s):  
Unsaturated Ketones ◽  
Conjugate Reduction

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.

scholarly journals Second Generation Synthesis of the Neo-Clerodane Diterpenoid Methyl Barbascoate

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Hisahiro Hagiwara ◽  
Naomi Honma ◽  
Kimihiko Kinugawa ◽  
Shota Sato ◽  
Takashi Hoshi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Second Generation ◽  
Samarium Diiodide ◽  
Conjugate Reduction ◽  
Palladium Catalyzed ◽  
Clerodane Diterpenoid

The second generation total synthesis of the neo-clerodane diterpenoid, methyl barbascoate, was accomplished in seven or nine linear steps via double enol triflation and subsequent palladium catalyzed double carbonylation, followed by regioselective samarium diiodide mediated conjugate reduction.

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