Enantioselective Rauhut-Currier-Type 1,6-Conjugate Addition of Methyl Vinyl Ketone to para -Quinone Methides

2017 ◽  
Vol 23 (27) ◽  
pp. 6509-6513 ◽  
Author(s):  
Tian-Chen Kang ◽  
Lu-Ping Wu ◽  
Qi-Wen Yu ◽  
Xin-Yan Wu
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.


2005 ◽  
Vol 16 (3b) ◽  
pp. 607-613 ◽  
Author(s):  
Humberto V. Fajardo ◽  
Luiz F. D. Probst ◽  
Antoninho Valentini ◽  
Neftalí L. V. Carreño ◽  
Adeilton P. Maciel ◽  
...  

2000 ◽  
Vol 65 (5) ◽  
pp. 797-804 ◽  
Author(s):  
Martina Havelková ◽  
Martin Studenovský ◽  
Dalimil Dvořák

The reaction of 6-iodo-, 9-benzyl-6-chloropurine and 7-benzyl-6-chloropurine with butyl acrylate, acrylonitrile, methyl vinyl ketone or methyl methacrylate under conditions of the Heck reaction in the presence of TlOAc or AgOAc afforded N1-alkylhypoxanthine derivatives. Formation of these unexpected products can be rationalised as a Tl+- or Ag+-assisted substitution of halogen with acetate anion. The 6-acetoxypurine derivative thus formed then eliminates ketene and gives 7-benzyl- or 9-benzylhypoxanthine. Conjugate addition of these compounds onto Michael acceptors furnishes the N1-substituted hypoxanthine derivatives.


1991 ◽  
Vol 47 (1) ◽  
pp. 329-336 ◽  
Author(s):  
Seizo Masuda ◽  
Keiji Minagawa ◽  
Masami Tanaka ◽  
Yutaka Asahi

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