ChemInform Abstract: Tandem Enantioselective Conjugate Addition-Mannich Reactions: Efficient Multicomponent Assembly of Dialkylzincs, Cyclic Enones and Chiral N-Sulfinimines.

ChemInform ◽  
2008 ◽  
Vol 39 (29) ◽  
Author(s):  
Jose C. Gonzalez-Gomez ◽  
Francisco Foubelo ◽  
Miguel Yus
2012 ◽  
Vol 53 (27) ◽  
pp. 3452-3455 ◽  
Author(s):  
Pavel A. Dub ◽  
Hui Wang ◽  
Masahito Watanabe ◽  
Ilya D. Gridnev ◽  
Takao Ikariya

ChemInform ◽  
2012 ◽  
Vol 43 (18) ◽  
pp. no-no
Author(s):  
Filip Bilcik ◽  
Michal Drusan ◽  
Jozef Marak ◽  
Radovan Sebesta

1988 ◽  
Vol 110 (16) ◽  
pp. 5411-5423 ◽  
Author(s):  
Malcolm R. Binns ◽  
Richard K. Haynes ◽  
Andrew G. Katsifis ◽  
Paul A. Schober ◽  
Simone C. Vonwiller

1989 ◽  
Vol 42 (10) ◽  
pp. 1785 ◽  
Author(s):  
RK Haynes ◽  
AG Katsifis ◽  
LM King ◽  
SC Vonwiller

The reactions of lithiated 1-(t-butylsulfinyl)prop-2-ene, 1-(t-butylsulfinyl)-3-methylbut-2-ene, 1-(t-butylsulfinyl)but-2-ene, 1-(phenylsulfinyl)but-2-ene and 2-methyl-1-(phenylsu1finyl)prop- 2-ene with methyl vinyl ketone, mesityl oxide and crotonaldehyde give largely carbonyl addition products arising from reaction through C1 or C3 of the allyl system. In the case of methyl crotonate, conjugate addition through C3 is observed. The initially formed diastereomers of the C1 adducts, allylic sulfoxides, are configurationally unstable. Only the lithiated 1-(t-butylsulfinyl)-3-methylbut-2-ene undergoes conjugate addition with methyl vinyl ketone to give an (E)-vinyl sulfoxide whose formation may involve the trans-decalyl transition state characteristic of the reactions of lithiated allylic sulfoxides with cyclic enones.


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