27829-72-7Relevant articles and documents
A convenient synthesis of amino acid-derived precursors to the important wine aroma 3-sulfanylhexan-1-ol (3SH)
Barker, David,Duhamel, Nina,Fedrizzi, Bruno,Jelley, Rebecca E.
, (2020)
A convenient, straightforward synthesis of the important amino acid-derived aroma precursors, 3-S-cysteinylhexan-1-ol (Cys-3SH) and 3-S-glutathionylhexan-1-ol (GSH-3SH) from commercially available butan-1-ol is reported. The versatility of this approach to include deuterium labelling is also demonstrated.
Synthesis of isotopically labelled thiol volatiles and cysteine conjugates for quantification of Sauvignon Blanc wine
Hebditch, Katherine R.,Nicolau, Laura,Brimble, Margaret A.
, p. 237 - 243 (2007)
The thiols 4-mercapto-4-methylpentan-2-ol (4MMPOH), 3-mercaptohexan-1-ol (3MH), and 3-mercaptohexyl acetate (3MHA), which contribute to the aroma profile of Sauvignon Blanc, as well as other varieties of wine, have been synthesized with deuterium labels. The cysteinylated precursors of the thiols, 4-(4-methylpentan-2-one)-L-cysteine (4MMP-cys) and 4-(4-methylpentan-2-ol)-L- cysteine (4MMPOH-cys), found in grape must were also synthesized with deuterium labels. These deuterated compounds provide useful internal standards for the quantification of these thiols in wine using LCMS. Copyright
Synthesis of alkyl sulfonic acid aldehydes and alcohols, putative precursors to important wine aroma thiols
Duhamel, Nina,Piano, Federico,Davidson, Samuel J.,Larcher, Roberto,Fedrizzi, Bruno,Barker, David
, p. 1728 - 1731 (2015)
The synthesis of the low molecular weight sulfonic acids, 2-methyl-4-oxopentane-2-sulfonic acid, 1-hydroxyhexane-3-sulfonic acid, 1-oxohexane-3-sulfonic acid and 1-hydroxyhexane-1,3-disulfonic acid from trans-2-hexenal and ethyl hex-2-enoate is reported. These sulfonic acids are putative precursors to the important wine aroma thiols, 3-mercaptohexan-1-ol, 3-mercaptohexyl acetate and 4-mercapto-4-methylpentan-2-one.
Visible-Light-Promoted Intramolecular α-Allylation of Aldehydes in the Absence of Sacrificial Hydrogen Acceptors
Liu, Feng,Liu, Jia-Li,tu, Jia-Lin
supporting information, p. 7369 - 7372 (2020/10/05)
We report herein an unprecedented protocol for radical cyclization of aldehydes with pendant alkenes via synergistic photoredox, cobaloxime, and amine catalysis. The transformation was achieved in the absence of external oxidants, providing a variety of 5-, 6-, and 7-membered ring products with alkene transposition in satisfactory yields. The reaction exhibits wide functional group compatibility and occurs under mild conditions with extrusion of H2.
Copper-Catalyzed Azide–Ynamide Cyclization to Generate α-Imino Copper Carbenes: Divergent and Enantioselective Access to Polycyclic N-Heterocycles
Chen, Yang-Bo,Deng, Chao,Liu, Rai-Shung,Liu, Xin,Luo, Chen,Wang, Ze-Shu,Ye, Long-Wu,Zhai, Tong-Yi,Zhang, Yi-Ping
supporting information, p. 17984 - 17990 (2020/08/21)
Here an efficient copper-catalyzed cascade cyclization of azide-ynamides via α-imino copper carbene intermediates is reported, representing the first generation of α-imino copper carbenes from alkynes. This protocol enables the practical and divergent synthesis of an array of polycyclic N-heterocycles in generally good to excellent yields with broad substrate scope and excellent diastereoselectivities. Moreover, an asymmetric azide–ynamide cyclization has been achieved with high enantioselectivities (up to 98:2 e.r.) by employing BOX-Cu complexes as chiral catalysts. Thus, this protocol constitutes the first example of an asymmetric azide–alkyne cyclization. The proposed mechanistic rationale for this cascade cyclization is further supported by theoretical calculations.
First synthesis of 3-S-glutathionylhexanal-d8 and its bisulfite adduct
Muhl, Jennifer R.,Pilkington, Lisa I.,Deed, Rebecca C.
supporting information, (2020/06/17)
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.
Oxidative esterification of aliphatic aldehydes and alcohols with ethanol over gold nanoparticle catalysts in batch and continuous flow reactors
Taketoshi,Ishida,Murayama, Toru,Honma, Tetsuo,Haruta, Masatake
, (2019/08/26)
Selective esterification of aliphatic aldehydes and alcohols with ethanol in the absence of a base is a more difficult reaction than that with methanol. Gold nanoparticles on ZnO were found to catalyze the oxidative esterification of octanal to ethyl octanoate with high selectivity. In addition, it was found that Au/ZnO was the most effective catalyst for yielding the desired ethyl ester without a base by direct esterification of 1-octanol with ethanol. As far as we know, this is the first report on oxidative esterification to give aliphatic ethyl esters from less reactive aliphatic alcohols and aldehydes without a base. The optimal size of gold NPs ranged from 2 to 6 nm and the presence of Au(0) was indispensable for this reaction. Au/ZnO exhibited the highest catalytic activity in both batch and flow reactors. The conversion was maintained for more than 20 h with 95% selectivity to the desired ethyl ester in the flow system.
Borane-Catalyzed Reductive α-Silylation of Conjugated Esters and Amides Leaving Carbonyl Groups Intact
Kim, Youngchan,Chang, Sukbok
supporting information, p. 218 - 222 (2016/01/25)
Described herein is the development of the B(C6F5)3-catalyzed hydrosilylation of α,β-unsaturated esters and amides to afford synthetically valuable α-silyl carbonyl products. The α-silylation occurs chemoselectively, thus leaving the labile carbonyl groups intact. The reaction features a broad scope of both acyclic and cyclic substrates, and the synthetic utility of the obtained α-silyl carbonyl products is also demonstrated. Mechanistic studies revealed two operative steps: fast 1,4-hydrosilylation of conjugated carbonyls and then slow silyl group migration of a silyl ether intermediate.
Asymmetric allylic alkylation of acyclic allylic ethers with organolithium reagents
Pérez, Manuel,Fa?anás-Mastral, Martín,Hornillos, Valentín,Rudolph, Alena,Bos, Pieter H.,Harutyunyan, Syuzanna R.,Feringa, Ben L.
supporting information, p. 11880 - 11883 (2012/10/29)
A highly efficient, regio- and enantioselective CuI/ phosphoramidite-catalyzed asymmetric allylic alkylation of allyl ethers with organolithium reagents is reported (see scheme). The use of organolithium reagents is essential for this catalytic C-C bond formation due to their compatibility with different Lewis acids. The versatility of allylic ethers under the copper-catalyzed reaction conditions with organolithium reagents is demonstrated in the shortest synthesis of (S)-Arundic acid. Copyright
Rh2(OAc)4/CeCl3-catalyzed olefination of carbonylferrocenes with α-diazocarbonyl compounds: A convenient synthesis of alkenylferrocenes
Chen, Shufeng,Zhang, Lele,Du, Yan,Li, Baoguo
experimental part, p. 943 - 947 (2012/06/04)
A concise and efficient protocol for the synthesis of al-kenylferrocene derivatives based on the olefination of carbonylferrocenes with α-diazocarbonyl compounds using Rh2(OAc)4/CeCl 3 as efficient catalysts was developed. The present method was applicable to many kinds of substituted carbonylferrocenes and α-diazocarbonyl compounds providing good to excellent yields of desired products. Georg Thieme Verlag Stuttgart · New York.
