42066-39-7

Upstream product

• 6165-76-0 propargyl p-toluenesulfonate 
• 677-22-5 tert-butylmagnesium chloride 
• 22688-39-7 (1R)-2-oxo-bornane-10-sulfonic acid (R)-1-tert-butyl-4,4-dimethyl-pent-2-ynyl ester 
• 2259-30-5 tert-butylmagnesium bromide 
• 109279-76-7 (R)(S)-1-bromo-4,4-dimethyl-1,2-pentadiene 
• 121887-80-7 Methanesulfonic acid (R)-1-tert-butyl-prop-2-ynyl ester 
• 51088-78-9 (2R)-2r,3t-di-tert-butyl-cyclopropanone (toluene-4-sulfonyl)-hydrazone 

Downstream Products

• 75805-75-3 [(Z)-1-(1-Chloro-2,2-dimethyl-propyl)-3,3-dimethyl-but-1-enylselanyl]-benzene 
• 56391-02-7 3-tert-Butyl-4-[2,2-dimethyl-prop-(E)-ylidene]-2,2-dimethyl-cyclobutanone 

Relevant academic research and scientific papers

Coupling of chiral 1-bromo-1,2-dienes with zinc-based cuprates: A new procedure for the regio and stereoselective synthesis of functionalized acetylenic compounds

Zinc alkylcyanocuprates (Knochel reagents) are found to be active in the cross-coupling reaction with allenic bromides affording acetylenic products with a high regio and stereoselective 1,3-anti substitution. The coupling process, which has been successf

Reaction of 1-bromo-1,2-dienes with alkylcuprates as a regio- and stereo-selective route to acetylenic or allenic compounds

Alkylcuprates react with 1-bromo-1,2-dienes to give allenic and/or acetylenic products.The selectivity of the crosscoupling is markedly dependent on the nature of the copper reagent, which plays a prominent role in determining both the regio- and the stereo-chemistry.The preparative aspects of these copper-induced reactions are discussed and their possible mechanism discussed.

Highly Stereoselective Synthesis of Chiral Alkylallenes by Organocopper(I)-Induced Anti 1,3-Substitution of Chiral Propynyl Esters

The synthesis of chiral 1,3-dialkylallenes R1CH=C=CHR2 of high enantiomeric purity, by applying homogeneous reaction between organocopper(I) reagents of type 2CuX>MgX-LiX> and chiral propynyl methanesulfonates or sulfinates at low temperatures in THF, is reported.The reactions are generally fast; typically complete conversion is obtained within a few minutes at -60 deg C.Overall, high anti stereoselectivity is observed.A plausible mechanism is put forward, and comparison is made with the stereochemistry of reactions of comparable substrates with d10 complexes, e.g. of Pd(0).

REACTIONS OF 3-ALKYL- AND 3,3-DIALKYL-1-BROMOALLENES WITH ORGANOCUPRATES: EFFECTS OF THE NATURE OF THE CUPRATE REAGENT ON THE REGIO- AND STEREOSELECTIVITY

Organocuprates induce 1,3- and direct substitution in 3-alkyl- and 3,3-dialkyl-1-bromo-1,2-dienes leading respectively to either terminal acetylenes or allenic hydrocarbons.The nature of the cuprate exerts a prominent role in determining both the regio- and the stereochemistry of these reactions.