220089-23-6

Upstream product

• 625-81-0 diisopropyl zinc 
• 104-55-2 3-phenyl-propenal 
• 86983-95-1 (1E)-4-methyl-1-phenylpent-1-en-3-ol 
• 123-62-6 propionic acid anhydride 
• 14371-10-9 (E)-3-phenylpropenal 
• 154081-22-8 (E)-styrylboronic acid 1,3-propandiol ester 
• 78-84-2 isobutyraldehyde 
• 870-46-2 t-butoxycarbonylhydrazine 
• 35661-51-9 N-(9-fluorenylmethyloxycarbonyl)hydrazine 
• 3160-32-5 (1E)-4-methyl-1-phenylpent-1-en-3-one 
• 100-52-7 benzaldehyde 
• 563-80-4 3-methyl-butan-2-one 
• 536-74-3 phenylacetylene 

Relevant academic research and scientific papers

Enantioselective addition of alkenylzinc reagents to aldehydes with organoboronates as the alkenyl source

Alkenylboronates were used as a vinyl source in the asymmetric addition of an alkenylzinc reagent to aldehydes catalyzed by a dendritic ligand. The resulting allylic alcohol products were obtained in 66-96% ee and 35-64% yields.

Asymmetric transfer hydrogenation of cycloalkyl vinyl ketones to allylic alcohols catalyzed by ruthenium amido complexes

A chemoselective 1,2-reduction of cycloalkyl vinyl ketones via asymmetric transfer hydrogenation is described. The reduction proceeded smoothly with a chiral diamine ruthenium complex as a catalyst and a HCOOH-NEt3 azeotrope as both a hydrogen source and solvent under mild conditions. A wide range of 1-cycloalkyl chiral allylic alcohols were obtained in good yields and up to 87% ee. It was found that the alkyl group plays an important role in the enantioselectivity.

Accessing Both Retention and Inversion Pathways in Stereospecific, Nickel-Catalyzed Miyaura Borylations of Allylic Pivalates

We have developed a stereospecific, nickel-catalyzed Miyaura borylation of allylic pivalates, which delivers highly enantioenriched α-stereogenic γ-aryl allylboronates with good yields and regioselectivities. Our complementary sets of conditions enable access to either enantiomer of allylboronate product from a single enantiomer of readily prepared allylic pivalate substrate. Excellent functional group tolerance, yields, regioselectivities, and stereochemical fidelities are observed. The stereochemical switch from stereoretention to stereoinversion largely depends upon solvent and can be explained by competitive pathways for the oxidative addition step. Our mechanistic investigations support a stereoretentive pathway stemming from a directed oxidative addition and a stereoinvertive pathway that is dominant when MeCN blocks coordination of the directing group by binding the nickel catalyst.

Kinetic Resolution of Racemic Allylic Alcohols by Catalytic Asymmetric Substitution of the OH Group with Monosubstituted Hydrazines

A new strategy has been established for the kinetic resolution of racemic allylic alcohols through a palladium/sulfonyl-hydrazide-catalyzed asymmetric OH-substitution under mild conditions. In the presence of 1 mol % [Pd(allyl)Cl]2, 4 mol % (S)-SegPhos, and 10 mol % 2,5-dichlorobenzenesulfonyl hydrazide, a range of racemic allylic alcohols were smoothly resolved with selectivity factors of more than 400 through an asymmetric allylic alkylation of monosubstituted hydrazines under air at room temperature. Importantly, this kinetic resolution process provided various allylic alcohols and allylic hydrazine derivatives with high enantiopurity.

Enantioselective acyl transfer catalysts and their use in kinetic resolution of alcohols and desymmetrization of meso-diols

Novel enantioselective acylation catalysts comprising chiral derivatives of DHIP and DHIQ, having the following representative general structures are disclosed: These new compounds are useful for resolving racemates or further enhancing the enantiomeric excess of an enantiomerically enriched composition and for desymmetrizing meso compounds.

Highly enantio- and diastereoselective tandem generation of cyclopropyl alcohols with up to four contiguous stereocenters

Three highly enantio- and diastereoselective one-pot procedures for the synthesis of cyclopropyl and iodocyclopropyl alcohols with up to four contiguous stereocenters are reported. Route 1 involves asymmetric addition of an alkylzinc reagent to an enal fo

Kinetic resolution of alcohols using a 1,2-dihydroimidazo[1,2-a]quinoline enantioselective acylation catalyst

(Chemical Equation Presented) A new enantioselective acylation catalyst (CI-PIQ), designed to provide enhanced π-stacking with benzylic and cinnamyl alcohol substrates, was found to give considerably increased reaction rates and selectivities compared with the first-generation catalyst CF3-PIP.

Asymmetric conjugate addition of organozinc compounds to α,β-unsaturated aldehydes and ketones with [2.2] paracyclophaneketimine ligands without added copper salts

(Chemical Equation Presented) The ligand makes it possible: The asymmetric conjugate addition of diethylzinc to α,β-unsaturated aldehydes and ketones occurs with catalytic amounts of the paracyclophaneketimine ligand 1 without further additives.

Facile synthesis of chiral isopropyl carbinols with high enantiomeric excess via catalytic enantioselective addition of diisopropylzinc to aldehydes

Highly effective syntheses of chiral alkyl and aryl isopropyl carbinols with high enantiomeric excess (94-98% ee) via catalytic enantioselective addition of diisopropylzinc to aldehydes have been developed.