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
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.
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).
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.
