27829-71-6Relevant academic research and scientific papers
First synthesis of 3-S-glutathionylhexanal-d8 and its bisulfite adduct
Muhl, Jennifer R.,Pilkington, Lisa I.,Deed, Rebecca C.
, (2020)
3-Sulfanylhexan-1-ol (3SH) is an impact odorant of white wines, imparting tropical fruit aromas. A reliable synthetic pathway to 3-S-glutathionylhexanal (glut-3SH-al), a precursor to 3SH that has not been intensively studied, was developed starting from 1-butanol. Application of this synthesis to 1-butanol-d10, conserved eight deuteriums, producing glut-3SH-al-d8, which can be used as an internal standard for future work on the occurrence and evolution of glut-3SH-al in wine systems. Additionally, both glut-3SH-SO3 and glut-3SH-SO3-d8 were synthesised from the corresponding aldehyde, enabling further study of the role of these bisulfite adducts in 3SH biogenesis.
N-acyl-5,5-dimethyloxazolidin-2-ones as latent aldehyde equivalents
Bach, Jordi,Blachere, Cecile,Bull, Steven D.,Davies, Stephen G.,Nicholson, Rebecca L.,Price, Paul D.,Sanganee, Hitesh J.,Smith, Andrew D.
, p. 2001 - 2010 (2007/10/03)
A study of the properties of N-hydrocinnamoyl- derivatives of 5,5-dimethyloxazolidin-2-one, 4,4-dimethyloxazolidin-2-one and oxazolidin-2-one upon hydride reduction with DIBAL-H demonstrates that the 5,5-dimethyl-group is essential for inhibition of endocyclic nucleophilic attack. For instance, treatment of N-hydrocinnamoyl-5,5-dimethyl-oxazolidin-2-one with DIBAL-H results in the selective formation of the stable N-1′-hydroxyalkyl derivative which may be regarded as a masked hydrocinnamaldehyde equivalent, as treatment under basic conditions affords the parent aldehyde in excellent yield. Treatment of N-hydrocinnamoyl-4,4-dimethyloxazolidin-2-one with DIBAL-H under identical conditions affords a complex mixture of products, including the formate ester product of endocyclic cleavage. As an alternate strategy, DIBAL-H reduction of straight chain and branched N-acyl-5,5-dimethyloxazolidin-2-one derivatives, followed by a Horner-Wadsworth-Emmons reaction affords α,β-unsaturated esters in good yields. Branching α- to the exocyclic carbonyl in N-acyl-oxazolidinones inhibits DIBAL-H reduction, but this can be overcome by precomplexation with ZnCl2, with subsequent fragmentation generating either the corresponding aldehyde or α,β-unsaturated esters. The addition of ZnCl2 has been shown to increase the diastereoselectivity observed in Wadsworth-Horner-Emmons reactions of lithiated phosphonates.
N-acyl-5,5-dimethyl-oxazolidin-2-ones as latent aldehyde equivalents
Bach, Jordi,Bull, Steven D.,Davies, Stephen G.,Nicholson, Rebecca L.,Sanganee, Hitesh J.,Smith, Andrew D.
, p. 6677 - 6680 (2007/10/03)
N-acyl-5,5-dimethyl-oxazolidin-2-ones can function as versatile latent aldehyde equivalents - reductive cleavage with DIBAL-H affords aldehydes in good yield, while tandem DIBAL-H/Wittig methodology affords α,β-unsaturated esters.
1,3-Dimethyl 2-oxo 1,3,2-diazaphospholidine precursor of (Z) α,β-unsaturated esters
Patois,Savignac
, p. 1317 - 1320 (2007/10/02)
α,β-Unsaturated esters of (Z) geometry are selectively obtained from cyclic phosphonocarboxylates derived from N,N'-dimethylethylenediamine.
THE EFFECT OF THE PHOSPHORYL SUBSTITUENTS ON THE STEREOCHEMISTRY OF THE HORNER REACTION
Larsen, Rolf Olaf,Aksnes,Gunnar
, p. 339 - 344 (2007/10/02)
The stereochemistry of the olefin forming reaction of various phosphoryl stabilized carbanions and aldehydes in ethanol is reported.The aromatic aldehydes react with acyclic phosphoryl stabilized carbanions yielding the trans isomers stereoselectively, whereas the 5- and 6-membered cyclic phosphonates (II and III) resulted in high yields of cis isomeric olefins.The aliphatic aldehydes give rise to considerable amounts of cis olefins also, decreasing in the series phosphonates, phosphinates and phosphine oxides, respectively.The stereochemical results are discussed in terms of pentacoordinated reaction intermediates.
