36713-66-3

Upstream product

• 24406-16-4 lithium di-n-butylcuprate 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 
• 40673-45-8 Butylbariumjodid 
• 64847-78-5 (E)-1,1-diacetoxy-3-phenylprop-2-ene 
• 82263-47-6 (2S,3R,4S,5R)-3,4-Dimethyl-5-phenyl-2-((E)-styryl)-oxazolidine 
• 115755-22-1 2-phenyl-1-(2-thiazolyl)-hexane 
• 74-88-4 methyl iodide 
• 109-72-8 n-butyllithium 
• 69375-96-8 trans-cinnamaldehyde ethylimine 
• 15286-54-1 1-cyclohexyl-4-phenyl-1-azabuta-1,3-diene 
• 77499-85-5 (E)-N-(3-phenylprop-2-en-1-ylidene)isopropylamine 
• 109-65-9 1-bromo-butane 
• 82215-31-4 (4S,5R)-3,4-Dimethyl-5-phenyl-2-((E)-styryl)-oxazolidine 

Downstream Products

• 114376-30-6 3-Phenyl-1-heptanol 
• 75834-22-9 (3R)-3-phenylheptan-1-ol 
• 137623-81-5 (3S)-3-phenylheptan-1-ol 

Relevant academic research and scientific papers

Dichotomy within 1,4-addition of organolithium and Grignard reagents to α,β-unsaturated Fischer alkoxycarbenes: A new synthesis of Fischer carbenes

The reaction of organolithium and Grignard reagents with pentacarbonyl[(ethoxy)(2-phenylethenyl)carbene]chromium(0) gave, after the quenching of the initially formed product of the 1,4-addition, different products depending on the organometallic and quenching reagents used. The addition of organolithiums, followed by a work-up with acid (AcOH or HCl), afforded the corresponding carbene complexes. In contrast, quenching the reaction mixture with ethanol led to the stereoselective formation of (Z)-enol ethers. The usage of Grignard reagents led to the formation of the carbene complexes regardless of which quenching reagent was used.

Alkylation of unsaturated aldehyde and allylic bisacetate with organomanganese reagents in presence of tetrakis acetonitrile copper(I) tetrafluroborate

The conjugate addition of organomanganese reagents to α,β- unsaturated aldehydes and allylic bisacetate in presence of Me3Si-Cl and tetrakis acetonitrile copper(I) tetrafluroborate is described. Copyright Taylor & Francis, Inc.

The copper mediated Barbier reactions of α,β-unsaturated ketones: Regioselective conjugate and 1,2-addition

The one-pot reaction of isophorone and other α,β-unsaturated ketones with alkyl and aryl halides in the presence of magnesium and a copper salt ('Barbier' conditions) leads to the regiospecific formation of 1,4-addition products; the use of lithium leads to regioselective 1,2-addition.

Regioselective addition reaction of organolanthanide reagents to α,β-unsaturated imines

Organolanthanum reagents[RLaCl2] generated in situ from LaCl3 and alkyl lithium or allyl magnesium could undergo a highly regioselective 1,2-addition to N-alkyl α,β-unsaturated imines, which provided a new and useful approach to synthesize allyl amines with good yields and high regioselectivity. Furthermore, for N-chiral alkyl α,β-unsaturated imine, in the case of n-butyl lithium, the diastereoselectivity achieved highly 90%.

Evaluation of several fluorinated ATPH derivatives as functionalized Lewis acid receptors for conjugate alkylation to α,β-unsaturated aldehydes with alkyllithium nucleophiles

Several fluorinated aluminum tris(2,6-diphenylphenoxide) (ATPH) derivatives have been synthesized to evaluate, as functionalized Lewis acid receptors, the conjugate alkylation ability to α,β-unsaturated aldehydes by the combined use of alkyllithium nucleo

Conjugate allylation to α,β-unsaturated aldehydes with the new chemzyme p-F-ATPH

Success at last: The 1,4-allylation of α,β-unsaturated aldehydes with selectivities up to 95/5 and yields of 83% has been achieved thanks to the newly developed Lewis acidic receptor p-F-ATPH (L= 2,6-(p-FC6H4)2C6H3O). In addition to a coordination site for the aldehyde, this possesses an appropriate coordination site for a reactive nucleophile, as shown schematically on the right.

THIAZOLYLMETHYLENETRIPHENYLPHOSPHORANE AND ITS BENZO DERIVATIVE: STABLE AND PRACTICAL WITTIG REAGENTS FOR THE SYNTHESIS OF VINYLTHIAZOLES AND VINYLBENZOTHIAZOLES. TWO-CARBON HOMOLOGATION OF ALDEHYDES.

The title thiazolyl phosphorane is a stable yet quite reactive Wittig-type reagent which uppon reaction with various aldehydes affords vinylthiazoles, mainly or exclusively as E-isomers, in very good yields.Also the benzothiazolyl phosphorane derivative, unlike a literature report, prove to react with aldehydes.Vinylthyazoles subjected to formyl deblocking from thiazole nucleous afford two-carbon homologated satured aldehydes.As an example, one of these vinylthiazoles, viz. the β-phenyl derivative 8f, proves to add n-butyl lithium cuprate to give after the formyl deblocking 3-phenylheptanal.

ADDITION D'ORGANOCUPRATES AUX OXAZOLIDINES CHIRALES α-β ETHYLENIQUES : I - RESULTATS - EFFETS DE SEL ET DE SOLVANT

Organocuprates add quantitatively to oxazolidines I.The steric course of the reaction can be reversed and the diastereoselectivity enhanced by salt effect and (or) by solvent effect.

ADDITION DIASTEREOSELECTIVE D'ORGANOCUPRATES A UNE OXAZOLIDINE CHIRALE α,Β INSATUREE: EFFET DE SOLVANT ET APPLICATION DES RESULTATS DE LA RMN 1H A LA DETERMINATION DE LA CONFIGURATION ABSOLUE ET DE LA PURETE OPTIQUE D'ARYL-3-ALKANALS

Addition of lithium dimethylcuprate to the chiral oxazolidine (1) in ether or in hexane leads to 3-phenylbutanals having the S or R configuration, respectively, with high optical yield in the latter case (e.e. = ca. 80percent).The 1H NMR study of the intermediate oxazolidine allows accurate determination of the optical yield and could be applied to the determination of the absolute configuration and optical purity of other 3-arylalkanals.