463304-45-2Relevant academic research and scientific papers
Diastereoselective addition of monoorganocuprates to a chiral fumarate: reaction development and synthesis of (-)-dihydroprotolichesterinic acid
Hethcox, J. Caleb,Shanahan, Charles S.,Martin, Stephen F.
, p. 6361 - 6368 (2015/08/18)
Abstract Recent studies of diastereoselective conjugate additions of monoorganocuprates, Li[RCuI], to chiral γ-alkoxycrotonates and fumarates are disclosed. This methodology was applied to the shortest total synthesis of (-)-dihydroprotolichesterinic acid
Highly diastereoselective conjugate additions of monoorganocopper reagents to chiral imides
Dambacher, Jesse,Anness, Robert,Pollock, Patrick,Bergdahl, Mikael
, p. 2097 - 2110 (2007/10/03)
Stereoselective conjugate additions to chiral N-enoyl amides employing various monoorganocuprate reagents, Li[RCuI], are described. The presence of TMSI in the addition of Li[RCuI] in THF provided the highest stereoselectivities. Reversed major diastereom
The Remarkable Ability of Lithium Ion to Reverse the Stereoselectivity in the Conjugate Addition of Li[BuCuI] to a Chiral N-Crotonyl-2-oxazolidinone
Dambacher, Jesse,Bergdahl, Mikael
, p. 3539 - 3541 (2007/10/03)
Equation presented. The influence of lithium ions on the conjugate addition of the monoorganocuprate reagent, Li[BuCuI], to a chiral crotonate has been investigated. The results show that iodotrimethylsilane (TMSI) is crucial for the asymmetric conjugate addition of the copper reagent, but only in THF or when 12-crown-4 is used. The reaction is thought not to involve any halosilane in any critical steps in the organocopper mechanisms conducted in Et 2O.
Asymmetric conjugate additions of TMSI promoted monoorganocuprate reagents, Li[RCuI], to various N-enoyl oxazolidinones
Pollock, Patrick,Dambacher, Jesse,Anness, Robert,Bergdahl, Mikael
, p. 3693 - 3697 (2007/10/03)
Diastereoselective conjugate additions to different α,β-unsaturated N-acyl oxazolidinones using various monoorganocuprate reagents, Li[RCuI], are described. The TMSI activated conjugate addition reactions provided high yields (80-98%) and reversed major d
