Aprotic conjugate addition of allyllithium reagents bearing polar groups to cyclic enones. 1. 3-Alkylallyl systems

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

Aprotic conjugate addition of allyllithium reagents bearing polar groups to cyclic enones. 2. 2-Alkyl-, 2,3-dialkyl- and 1,3-dialkylallyl systems

1988 ◽  
Vol 110 (16) ◽  
pp. 5423-5433 ◽  
Author(s):  
Richard K. Haynes ◽  
Andrew G. Katsifis ◽  
Simone C. Vonwiller ◽  
Trevor W. Hambley
Keyword(s):  
Conjugate Addition ◽  
Polar Groups ◽  
Cyclic Enones

ChemInform Abstract: Aprotic Conjugate Addition of Allyllithium Reagents Bearing Polar Groups to Cyclic Enones. Part 1. 3-Alkylallyl Systems.

ChemInform ◽  
1988 ◽  
Vol 19 (49) ◽  
Author(s):  
M. R. BINNS ◽  
R. K. HAYNES ◽  
A. G. KATSIFIS ◽  
P. A. SCHOBER ◽  
S. C. VONWILLER
Keyword(s):  
Conjugate Addition ◽  
Polar Groups ◽  
Cyclic Enones

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

Aprotic Conjugate Addition Reactions of Lithiated Allylic Sulfoxides With Acyclic Enones; a Breakdown of the trans-Decalyl Transition State

1989 ◽  
Vol 42 (10) ◽  
pp. 1785 ◽  
Author(s):  
RK Haynes ◽  
AG Katsifis ◽  
LM King ◽  
SC Vonwiller
Keyword(s):  
Transition State ◽  
Conjugate Addition ◽  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
Mesityl Oxide ◽  
Addition Reactions ◽  
State Characteristic ◽  
Methyl Vinyl ◽  
Cyclic Enones ◽  
Carbonyl Addition

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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