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Search for "1,3-dithiane" in Full Text gives 11 result(s) in Beilstein Journal of Organic Chemistry.
1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures
Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12
- (hetero)aromatic building blocks. 1,4-Dithianes have as yet not been investigated to the same extent as their well-known 1,3-dithiane counterparts, but they do offer attractive transformations that can find good use in the assembly of a wide array of complex molecular architectures, ranging from lipids
- , and several excellent reviews have highlighted their synthetic versatility and utility in the assembly of complex target molecules [4][5][6]. Some recent examples of 1,3-dithiane-mediated short and efficient total syntheses of complex target products are shown in Scheme 1b [7], wherein the original
- ] and b) recent applications in the total synthesis of complex target products (original attachment place of 1,3-dithiane ‘scaffolding’ groups shown with dashed purple lines) [7][8][9][10][11]. Metalation of other saturated heterocycles is often problematic due to β-elimination [16][17]. Thianes as
Synthetic study toward tridachiapyrone B
Beilstein J. Org. Chem. 2022, 18, 1741–1748, doi:10.3762/bjoc.18.183
- chiral tetrahydrofuran (Scheme 1b). To assemble the skeleton of the natural product, we developed a new strategy in which the α,α’-dimethoxy-γ-pyrone motif 2 was first desymmetrized by a sequence encompassing the conjugate addition of 2-lithio-1,3-dithiane, elimination of methoxide lithium, and
- deprotonation of 2-(α’-methoxy-γ-pyrone)-1,3-dithiane. The resulting vinylogous enolate intermediate was trapped with the electrophile 3, amounting to the one-pot preparation of compound 4, having a masked carbonyl function connecting both key fragments [27][28]. Isolated and characterized by Schmitz [17], the
- temperature in contrast with the nucleophile 2-lithio-1,3-dithiane, and with acetic acid as electrophile (Scheme 3). Among the possible isomers that can be expected, a single one 6a’ was isolated in 49% yield after trituration, as it was found rather unstable on silica gel. While the addition of more reactive
Electrophilic oligodeoxynucleotide synthesis using dM-Dmoc for amino protection
Beilstein J. Org. Chem. 2019, 15, 1116–1128, doi:10.3762/bjoc.15.108
- electrophilic oligodeoxynucleotides (ODNs) was achieved using dimethyl-Dmoc (dM-Dmoc) as amino protecting group. Due to the high steric hindrance of the 2-(propan-2-ylidene)-1,3-dithiane side product from deprotection, the use of excess nucleophilic scavengers such as aniline to prevent Michael addition of the
- steps from 1,3-dithiane (6) according to a procedure we reported previously [44]. The dC phosphoramidite monomer 3a was synthesized from compound 9 [45]. The formation of the hindered O-tert-alkyl N-arylcarbamate 10 was found highly challenging [44][46][47]. We tried many conditions and finally found
- not caused by premature oxidation of the dM-Dmoc groups by iodine in the oxidation step in ODN synthesis because the problem did not exist when Dmoc was used for ODN synthesis [41]. In addition, we also subjected 1,3-dithiane to the iodine oxidation conditions for over 24 hours, no oxidation could be
An amine protecting group deprotectable under nearly neutral oxidative conditions
Beilstein J. Org. Chem. 2018, 14, 1750–1757, doi:10.3762/bjoc.14.149
- 10.3762/bjoc.14.149 Abstract The 1,3-dithiane-based dM-Dmoc group was studied for the protection of amino groups. Protection was achieved under mild conditions for aliphatic amines, and under highly reactive conditions for the less reactive arylamines. Moderate to excellent yields were obtained
- carboxylic acid protection [19]. To further explore the use of the 1,3-dithiane function as protecting group in organic synthesis, here we report the results of our studies on the use of the dimethyl-1,3-dithian-2-ylmethoxycarbonyl (dM-Dmoc) group for amine protection (Scheme 1). Compared with the Dmoc group
- of Dmoc due to its higher steric hindrance. Such side reactions could be a serious issue in some situations [18]. Results and Discussion To protect amines, compound 4 was prepared readily by reacting deprotonated 1,3-dithiane with acetone followed by treating with p-nitrophenylchloroformate (see
A selective removal of the secondary hydroxy group from ortho-dithioacetal-substituted diarylmethanols
Beilstein J. Org. Chem. 2018, 14, 1229–1237, doi:10.3762/bjoc.14.105
- % yields and is recommended for the substrates containing sulfur atoms, for which transition metal-induced reactions fail. Keywords: diarylmethanes; diarylmethanols; 1,3-dithiane; selective reduction; sodium cyanoborohydride; zinc iodide; Introduction In last decades, diarylmethanes, such as I–IV and
- -coupling reactions of substrates containing an 1,3-dithiane moiety are feasible, like in the case of the 2-arylation of 2-aryl-substituted 1,3-dithianes. However, in the case of 2-benzyl-substituted 1,3-dithianes, a tandem elimination/1,3-dithiane ring opening followed by a Pd-catalyzed C−S bond formation
The chemistry and biology of mycolactones
Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159
Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition
Beilstein J. Org. Chem. 2017, 13, 762–767, doi:10.3762/bjoc.13.75
- base organocatalyzed addition (Scheme 1). This reaction would lead to bicyclic systems with the salient attribute of having a convex-concave facial differentiation, allowing subsequent diastereoselective transformations. With the aim of using a dithiane nucleophile, we selected 1,3-dithiane-2
- -carboxylic acid because of its relatively low pKa (compared with non-carboxylate substituted analogs) and the possibility of using an ester linkage as a tether. We found that the heretofore unknown dicyclohexylcarbodiimide (DCC) mediated coupling between para-quinols and 1,3-dithiane-2-carboxylic acid
Sacrolide A, a new antimicrobial and cytotoxic oxylipin macrolide from the edible cyanobacterium Aphanothece sacrum
Beilstein J. Org. Chem. 2014, 10, 1808–1816, doi:10.3762/bjoc.10.190
- because of epimerization [12]. To circumvent this problem, we initially attempted to protect the ketone group prior to chemical conversion (Scheme 1). Compound 1 was acetylated (Supporting Information File 1) and subjected to protection as 1,3-dithiane [13] or 1,4-dinitrophenylhydrazone [14]; however
Re2O7-catalyzed reaction of hemiacetals and aldehydes with O-, S-, and C-nucleophiles
Beilstein J. Org. Chem. 2013, 9, 1526–1532, doi:10.3762/bjoc.9.174
- furnish a dithioacetal or a 1,3-dithiane. A ketone substrate did not react under these conditions (not shown). The mono- and dithioacetalization reactions were visibly different from the O-acetalizations described above. Whereas addition of Re2O7 to a hemiacetal in the presence of an alcohol generates a
Alternaric acid: formal synthesis and related studies
Beilstein J. Org. Chem. 2013, 9, 166–172, doi:10.3762/bjoc.9.19
- insufficient for adequate stereocontrol in the three-component coupling reaction [34]. An additional branch point in the carbon backbone, such as in 16b, was deemed necessary. The 1,3-dithiane group in aldehyde 16ba was conceived as a promising candidate for a stereocontrolling element due to its large size
Metathesis access to monocyclic iminocyclitol-based therapeutic agents
Beilstein J. Org. Chem. 2011, 7, 699–716, doi:10.3762/bjoc.7.81
- steps via the Fleet protocol [55]. The tandem RCM/dihydroxylation sequence was also applied by Davis et al. in the synthesis of (−)-2,3-trans-3,4-cis-dihydroxyproline. In this case, an α-amino aldehyde, prepared by addition of a 1,3-dithiane to a chiral N-sulfinyl imine, was used as the chiral starting
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