478930-85-7

Upstream product

• 7103-09-5 4-but-1-enylmagnesium bromide 
• 4392-24-9 Cinnamyl bromide 
• 5162-44-7 1-bromo-4-butene 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 

Relevant academic research and scientific papers

Synthesis and use of a phosphoramidite ligand for the copper-catalyzed enantioselective allylic substitution. Tandem allylic substitution/ring-closing metathesis

A new one-pot method of reductive amination is used to prepare a chiral C2 symmetrical amine. This amine is used for the synthesis of a new chiral phosphoramidite ligand. The new ligand is, in turn, used to illustrate the enantioselective copper-catalyzed

Improvements and Applications of the Transition Metal-Free Asymmetric Allylic Alkylation using Grignard Reagents and Magnesium Alanates

Two new N-heterocyclic carbene (NHC) ligands have been synthesized and employed in the transition metal-free asymmetric allylic alkylation (AAA) mediated by Grignard reagents and magnesium alanates. The employment of these ligands showed high yields and improved regio- and enantioselectivity in the formation of tertiary and quaternary stereocenters. Moreover, the low catalyst loading (up to 0.3 mol%) and high scalability (up to 10 mmol) of this improved methodology provide a convenient access to biologically active compounds and synthetically valuable intermediates.

Bidentate hydroxyalkyl NHC ligands for the copper-catalyzed asymmetric allylic substitution of allyl phosphates with grignard reagents

Demonstrating their potential: Bidentate alkoxy NHC ligands have been used in the copper-catalyzed asymmetric allylic alkylation of allyl phosphates with Grignard reagents (see scheme). The method provides access to tertiary and quaternary chiral centers with high regio- and enantioselectivity. The system is also applied to the synthesis of chiral E,E-dienes, a key structural motif prevalent in natural products. Copyright

A highly effective phosphoramidite ligand for asymmetric allylic substitution

Very high enantioselectivity has been achieved both in the copper-catalyzed alkylation of allylic substrates by Grignard and organozinc reagents and in the iridium-catalyzed animation of cinnamyl carbonate by employing a very efficient phosphoramidite ligand (see scheme).

Tandem copper-catalyzed enantioselective allylation-metathesis

(matrix presented) Grignard reagents undergo enantioselective (up to 86% ee) copper-catalyzed SN2′ substitution on achiral allylic chlorides. The reaction is wide in scope for both the Grignard reagent and the allylic substrate. The resulting terminal alkene could be submitted to intra-or intermolecular metathesis to afford new chiral synthons. The experimental conditions are compatible with a one-pot overall substitution - metathesis procedure without loss of enantioselectivity.