69824-92-6

Upstream product

• 930-68-7 cyclohexenone 
• 628-17-1 amyl iodide 
• 64889-46-9 n-pentylcopper 
• 14402-93-8 dipentylzinc 
• 5771-58-4 bicyclo[4.1.0]heptan-2-one 
• 72665-98-6 n-pentylzinc iodide 
• 1291093-59-8 1-methoxy-5-pentylcyclohexa-1,4-diene 

Downstream Products

• 73959-37-2 (3R)-n-pentyl-cyclohexanone 
• 73959-36-1 (3S)-n-pentyl-cyclohexanone 

Relevant academic research and scientific papers

1,5-ADDITION OF DIALKYLCUPRATE REAGENTS TO ALKYLCYCLOPROPYL KETONES

Cyclopropyl ketones undergo 1,5-addition at the less substituted carbon using the complex reagent R2CuCNLi2*BF3.

Regioselective Iridium-Catalyzed Asymmetric Monohydrogenation of 1,4-Dienes

A highly efficient regio- and enantioselective monohydrogenation of 1,4-dienes has been realized using an iridium catalyst with a chiral N,P-ligand under mild conditions. The substrate scope was studied and included both unfunctionalized as well as functionalized substituents on the meta- or para-position. Substrates having substituents with functionalities such as silyl protected alcohols or ketals were monohydrogenated in high regioselectivity and high enantiomeric excess (up to 98% ee).

Nickel (II) catalysed 1,4- addition reactions of functionalised organozinc reagents with enones

An efficient catalytic 1,4 addition reaction of functionalised organozinc reagents with enones has been developed using a nickel complex as catalyst.

Nickel-catalyzed cross-coupling between functionalized primary or secondary alkylzinc halides and primary alkyl halides

In the presence of Bu4NI (3 equiv) and 4-fluorostyrene (20 mol %), unreactive primary and secondary alkylzinc iodides undergo nickel-catalyzed cross-couplings with various primary alkyl iodides or bromides. More reactive secondary dialkylzincs and the mixed zinc organometallics RZnTMSM undergo the cross-coupling reaction in the absence of Bu4NI. The bicyclic secondary diorganozinc 6 prepared via boron-zinc exchange reacts with high retention of configuration. Free NH-groups are tolerated in the cross-coupling allowing the synthesis of aminated products.

Neopentyl and neophyl groups: New nontransferable groups for organocopper and organozinc chemistry

Neopentyl and Neophyl groups have been found to be excellent nontransferable groups for organozinc and organocopper chemistry. We have shown that mixed diorganozincs of the type FG-R-Zn(CH2CMe2R) can be used advantageously for the enantioselective addition to aldehydes. These mixed copper or zinc reagents are also found to be very efficient in the Michael addition to various activated alkenes.

A new method for synthesis of functionalized organozinc-copper(I) reagents and their 1,4-addition reaction with enones

The transmetalation of functionalized organozinc iodides with Cu(OAc)2 in THF provides a new convenient method for the preparation of functionalized organozinc-copper(I) reagents FG-RCu(OAc)ZnI which ultimately undergo 1,4- addition reaction wi

Uncatalyzed conjugate additions of diorganozincs in N- methylpyrrolidinone

Diorganozincs efficiently add to enones, unsaturated nitriles and nitroolefins in a mixture of THF and NMP furnishing the corresponding Michael adducts in good to excellent yields.

Ultrasound in organic syntheses. 19. Further studies on the conjugate additions to electron deficient olefins in aqeuous media

Alkyl halides add smoothly to a variety of olefinic bonds conjugated with electron withdrawing groups, in the presence of zinc-copper couple. Sonication enhances the efficiency of the process, which takes place in aqeuous media following, most probably, a radical pathway.

ORGANOCOPPER REAGENTS IN DIMETHYL SULFIDE

Organocopper(I) reagents, RCu, are both more stable and more reactive when prepared in dimethyl sulfide instead of ether or tetrahydrofuran.A wide range of Li reagents has been investigated with good results, as has a selection of Grignard reagents.Excellent yields of products are observed with typical substrates as α,β-unsaturated ketones and acid chlorides.

ULTRASOUND IN ORGANIC SYNTHESIS 16. OPTIMISATION OF THE CONJUGATE ADDITIONS TO α,β-UNSATURATED CARBONYL COMPOUNDS IN AQUEOUS MEDIA.

Optimisation of the conjugate addition of alkyl groups to α-enones under sonochemical conditions can be effected, especialy by a proper choice of the solvent, most probably because of its stuctural properties.