114409-87-9

Upstream product

• 109-72-8 n-butyllithium 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 124658-79-3 (E)-3,3-dimethyl-7-phenyl-2,4-dioxahept-6-ene 
• 109-65-9 1-bromo-butane 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 542-69-8 1-iodo-butane 
• 645-45-4 hydrocinnamic acid chloride 
• 2051-49-2 n-hexanoic anhydride 
• 159213-04-4 N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methylhexanamide 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 159213-08-8 (S)-2-Benzyl-hexanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 14980-86-0 N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-3-phenylpropanamide 
• 159345-10-5 (R)-2-benzyl-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methylhexanamide 
• 7500-73-4 (±)-2-benzyl-1-hexanol 

Downstream Products

• 159213-11-3 (R)-2-Benzyl-hexanal 
• 1116651-76-3 (4S,5R)-2-((S)-2-benzylhexylselanyl)-4-methyl-5-phenyl-4,5-dihydrooxazole 
• 7500-73-4 (2R)-2-Benzyl-1-hexanol 
• 5668-19-9 (2R)-2-Benzylhexanoic acid 
• 5668-19-9 (2S)-2-Benzylhexanoic acid 

Relevant academic research and scientific papers

Synthesis and olfactory evaluation of optically active β-alkyl substituted γ-lactones and whiskey lactone analogues

Optically active β-alkyl substituted γ-lactones and whiskey lactone analogues were synthesized, and the odor properties were evaluated. During the preparation of the chiral intermediates, we found good reaction conditions for the highly enantioselective esterification of 3-arylmethyl-2-methyl-1-propanols to kinetically resolve them. The results of the olfactory evaluations of the synthesized lactones revealed that the alkyl groups on the γ-lactone rings played an important role for the odor profiles.

Enantioselective Formal α-Methylation and α-Benzylation of Aldehydes by Means of Photo-organocatalysis

Detailed herein is the photochemical organocatalytic enantioselective α-alkylation of aldehydes with (phenylsulfonyl)alkyl iodides. The chemistry relies on the direct photoexcitation of enamines to trigger the formation of reactive carbon-centered radicals from iodosulfones, while the ground-state chiral enamines provide effective stereochemical control over the radical trapping process. The phenylsulfonyl moiety, acting as a redox auxiliary group, facilitates the generation of radicals. In addition, it can eventually be removed under mild reducing conditions to reveal methyl and benzyl groups.

Pseudoephenamine: A practical chiral auxiliary for asymmetric synthesis

Unrestricted: Pseudoephenamine is introduced as a versatile chiral auxiliary and an alternative to pseudoephedrine in asymmetric synthesis. It is free from regulatory restrictions and leads to remarkable stereocontrol in alkylation reactions, especially in those that form quaternary carbon centers. Amides derived from pseudoephenamine exhibit a high propensity to be crystalline substances, and provide sharp, well-defined signals in NMR spectra. Copyright

Asymmetric synthesis of α-alkylated aldehydes using terminal epoxide-derived chiral enamines

(Chemical Equation Presented) Effective discrimination: Efficient lithium amide-induced terminal epoxide-enamine transformation provides the first enamines capable of generating α-alkylated aldehydes with high asymmetric induction by intermolecular nucleophilic substitution (see scheme).

Evaluation of (+)-sparteine-like diamines for asymmetric synthesis

Three new (+)-sparteine-like diamines were prepared from (-)-cytisine and evaluated as sparteine surrogates in the α-lithiation rearrangement of cyclooctene oxide and the palladium(II)/diamine catalyzed oxidative kinetic resolution of 1-indanol. The new diamines exhibited opposite enantioselectivity to that observed with (-)-sparteine but increasing the steric hindrance of the N-alkyl group beyond N-Et had a detrimental effect on enantioselectivity. The optimal N-Me diamine was evaluated with much success in five other (-)-sparteine-mediated processes involving different metals (lithium, magnesium, and copper) and different types of reaction mechanisms.

Application of A Recyclable Pseudoephedrine Resin in Asymmetric Alkylations on Solid Phase

A pseudoephedrine resin has been successfully employed in asymmetric alkylations on solid phase. Immobilized pseudoephedrine amides are conveniently prepared by the one-step attachment of pseudoephedrine to Merrifield resin through the hydroxyl group and subsequent acylation on nitrogen. Deprotonation and alkylation of the resin-bound amides proceeds smoothly. Ketones and alcohols are cleaved from the resin in high enantiomeric excess and moderate to good overall yield. The parallel, asymmetric solid-phase synthesis of a small library of chiral ketones and alcohols has been carried out to illustrate the utility of the approach. Finally, the pseudoephedrine resin can be conveniently recycled and utilized with no significant loss in the yield or enantiomeric excess of the products.

An easy access to enantio-enriched α-substituted aldehydes by carbolithiation of β-phenyl or β-silyl-α,β-ethylenic aldehydes, protected with the monolithioamide of a chiral diamine

Lithium amide derived from N,N,N′-trimethyl-1,2-diphenylethanediamine converts cinnamaldehyde to a lithium alkoxyamide which undergoes a regio- and stereoselective carbolithiation upon addition of various organolithiums. Subsequent hydrolysis or trapping with MeI delivers α-mono-, or α,β-disubstituted 3-phenylpropanals with e.e.s of 76-96%. Extension to a silylated α-enal is possible.

Regioselective addition of nbutyllithium on secondary cinnamyl amides: 'Michael' versus 'contra-Michael' process

Lithiated secondary cinnamyl amides undergo a preferred 'contra-Michael' addition of nbutyllithium, complexed with (-)sparteine, in a non polar solvent.

Enantioselective carbometalation of cinnamyl derivatives: New access to chiral disubstituted cyclopropanes - Configurational stability of benzylic organozinc halides

A stoichiometric or catalytic amount of (-)-sparteine can serve asa promoter for the enantioselective carbolithiation of cinnamyl derivatives by primary and secondary organolithium compounds. The enantiofacial choice of the addition reaction is dependent on the stereochemistry of the initial double bond. The resulting benzylic organolithium compounds can be derivatized to a linear phenylated chain that bears two contiguous stereogenic centers with given configurations. The use of the dimethyl acetal of the (E)-cinnamyl alcohol allows the highest enantioselective carbolithiation and by simply warming the reaction mixture to room temperature, the resulting benzylic organo-lithium intermediate undergoes a 1,3-elimination to give the chiral disubstituted cyclopropane in high enantiomeric excess (90-95% ee). Another significant finding is the observation that the Li-Zn transmetalation in a benzylic species occurs with inversion of configuration, and the corresponding acyclic benzylic zinc halides have observable configurational stability at - 30°C.