75166-31-3Relevant academic research and scientific papers
A highly stereoselective organocatalytic approach to Lilial and muguesia
Gualandi, Andrea,Emma, Marcogiuseppe,Giacoboni, Jessica,Mengozzi, Luca,Cozzi, Piergiorgio
, p. 449 - 452 (2013/04/10)
The stereoselective alkylation of aldehydes with benzodithiolylium tetrafluoborate gave a straightforward access to key compounds for the synthesis of fragrances and flavors. Georg Thieme Verlag Stuttgart · New York.
An asymmetric hydroformylation catalyst that delivers branched aldehydes from alkyl alkenes
Noonan, Gary M.,Fuentes, Jose A.,Cobley, Christopher J.,Clarke, Matthew L.
supporting information; experimental part, p. 2477 - 2480 (2012/04/18)
Surprising selectivity: The first enantioselective hydroformylations of simple alkenes of type RCH2CH=CH2 to preferentially deliver the branched aldehyde product have been discovered using a new chiral ligand, named bobphos (see scheme). Established ligands are unselective in this reaction or show a slight preference towards the linear aldehyde. Copyright
Bioreduction of α-methylcinnamaldehyde derivatives: Chemo-enzymatic asymmetric synthesis of Lilial and Helional
Stueckler, Clemens,Mueller, Nicole J.,Winkler, Christoph K.,Glueck, Silvia M.,Gruber, Karl,Steinkellner, Georg,Faber, Kurt
experimental part, p. 8472 - 8476 (2011/01/10)
Nonracemic aryl-substituted α-methyldihydrocinnamaldehyde derivatives employed as olfactory principles in perfumes (Lilial, Helional) were obtained via enzymatic reduction of the corresponding cinnamaldehyde precursors using cloned and overexpressed ene-reductases. (R)-Enantiomers were obtained using the old-yellow-enzyme (OYE) homolog YqjM from Bacillus subtilis and 12-oxophytodienoic acid reductase isoenzyme OPR1 from tomato (e.e. max 53%), and (S)-aldehydes were furnished in up to 97% e.e. using isoenzyme OPR3, nicotinamide 2-cyclohexene-1-one reductase NCR from Zymomonas mobilis and yeast OYE isoenzymes 1-3 under optimised reaction conditions in the presence of t-butyl methyl ether as the co-solvent. The stereochemical outcome of the reduction of α-methylcinnamaldehyde using NCR and OYEs 1-3 [previously reported to be (R)] was unambiguously corrected to be (S).
Acid promoted CIDT for the deracemization of dihydrocinnamic aldehydes with Betti's base
Rosini, Goffredo,Paolucci, Claudio,Boschi, Francesca,Marotta, Emanuela,Righi, Paolo,Tozzi, Francesco
experimental part, p. 1747 - 1757 (2011/02/28)
Racemic α-epimerizable and unfunctionalized aldehydes have been converted into enantiomerically enriched mixtures through a sequence of (i) a conversion into the diastereoisomeric 3-substituted 1-phenyl-2,3-dihydro-1H- naphtho[1,2-e][1,3]oxazines by reaction with the (R)- or (S)-1-(α- aminobenzyl)-2-naphthol (Betti's base), (ii) an acid promoted crystallization-induced diastereoisomer transformation (CIDT), and (iii) a clean cleavage of the dihydro-1,3-naphthoxazinic ring of the enriched diastereoisomer, easily collected by filtration, allowing the recovery of the enantiomerically enriched aldehydes and the chiral auxiliary.
Synthesis and Properties of the Enantiomers of the Two Artificial Fragrances Lilial and Methylundecanal
Enders, Dieter,Dyker, Hubert
, p. 1107 - 1110 (2007/10/02)
The enantiomers of the two artificial fragrances 3-(4-tert-butylphenyl)-2-methylpropanal (lilial) and 2-methylundecanal are synthesized with high enantiomeric purity using the SAMP/RAMP hydrazone method.The enantiomeric excesses are determined by HPLC via the corresponding SASP hydrazones.The olfactorial qualities of the enantiomers are described.
