A simple, effective method for achieving high 1,4-relative asymmetric induction in carbonyl addition reactions

1991 ◽  
Vol 113 (9) ◽  
pp. 3608-3610 ◽  
Author(s):  
Gary A. Molander ◽  
Joseph P. Haar
Keyword(s):  
Asymmetric Induction ◽  
Addition Reactions ◽  
Carbonyl Addition

Preparation, Thermal Stability and Carbonyl Addition Reactions of 2,5-Difluorophenyl Lithium and 2,5-Difluorophenyl Grignard

Synlett ◽  
2004 ◽  
pp. 1646-1648 ◽  
Author(s):  
Jeremy P. Scott ◽  
Sarah E. Brewer ◽  
Antony J. Davies ◽  
Karel M. Brands
Keyword(s):  
Thermal Stability ◽  
Addition Reactions ◽  
Carbonyl Addition

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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