Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol

• Emine Salamci and
• Ayse Kilic Lafzi

Beilstein J. Org. Chem. 2022, 18, 1539–1543, doi:10.3762/bjoc.18.163

• cyclooctene endoperoxide, prepared by photooxygenation of cis,cis-1,3-cyclooctadiene, with zinc gave a cyclooctenediol and then benzylation of the hydroxy group yielded dibenzylated cyclooctene. Oxidation of the latter compound by OsO4/NMO followed by mesylation of the hydroxy group provided bis(benzyloxy

• cis,cis-1,3-cyclooctadiene. Results and Discussion The synthesis of the diol 5, which was prepared by reduction of the endoperoxide 4 with zinc was carried out as described in the literature [18]. Treatment of the diol 5 with benzyl bromide and NaH in DMF gave the corresponding (dibenzyloxy

• have achieved the synthesis of 3-aminocyclooctanetriol 13 and aziridinecyclooctanediol 16 starting from cis,cis-1,3-cyclooctadiene. The nitrogen functionalities were introduced by the substitution with NaN3 of the corresponding mesylate. Reduction of the azido functionalities gave monoaminocyclitol and

Efficient and regioselective synthesis of dihydroxy-substituted 2-aminocyclooctane-1-carboxylic acid and its bicyclic derivatives

• İlknur Polat,
• Selçuk Eşsiz,
• Uğur Bozkaya and
• Emine Salamci

Beilstein J. Org. Chem. 2022, 18, 77–85, doi:10.3762/bjoc.18.7

• . We have recently reported the synthesis of various eight-membered aminocyclitols and their derivatives [19][20][21][22][23][24][25]. In the present paper, we describe the synthesis of some hydroxylated β-amino acid derivatives containing eight-membered rings starting from cis,cis-1,3-cyclooctadiene

• . Results and Discussion Initially, we focused on the synthesis of β-lactam 2, which was prepared by the cycloaddition of chlorosulfonyl isocyanate (CSI) to cis,cis-1,3-cyclooctadiene, as described in the literature [26]. β-Lactam 2 was transformed into cis-amino ester 3 by cleavage of the lactam ring with

Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols

• Emine Salamci and
• Yunus Zozik

Beilstein J. Org. Chem. 2021, 17, 705–710, doi:10.3762/bjoc.17.59

• Emine Salamci Yunus Zozik Department of Chemistry, Faculty of Sciences, Atatürk University, 25240 Erzurum, Turkey 10.3762/bjoc.17.59 Abstract The efficient synthesis of two new stereoisomeric 3-aminocyclooctanetriols and their new halocyclitol derivatives starting from cis,cis-1,3-cyclooctadiene

• are reported. Reduction of cyclooctene endoperoxide, obtained by photooxygenation of cis,cis-1,3-cyclooctadiene, with zinc yielded a cyclooctene diol followed by acetylation of the hydroxy group, which gave dioldiacetate by OsO4/NMO oxidation. The cyclooctane dioldiacetate prepared was converted to

• of two new 3-aminocyclooctanetriols and some chlorinated C8-cyclitols starting from cis,cis-1,3-cyclooctadiene. Results and Discussion For the synthesis of amino- and chlorocyclitols and their derivatives, we first selected endoperoxide 5 as the starting molecule, which was prepared using a procedure

Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes

• Savva A. Ponomarev,
• Roman V. Larkovich,
• Alexander S. Aldoshin,
• Andrey A. Tabolin,
• Sema L. Ioffe,
• Jonathan Groß,
• Till Opatz and
• Valentine G. Nenajdenko

Beilstein J. Org. Chem. 2021, 17, 283–292, doi:10.3762/bjoc.17.27

• (H5 or H6) and its coupling constant to fluorine (3JH5-F or 3JH6-F). The reaction with 7- and 8-membered cyclic dienes (1,3-cycloheptadiene and 1,3-cyclooctadiene) did not result in the formation of the corresponding cycloadducts confirming that the reaction is very sensitive to the structure of the

• monofluorinated bicyclo[2.2.2]oct-2-enes was obtained in up to 40% yield. The reactivity of CPD and its homologues was evaluated and compared. The reaction rate for CHD proved to be 267 times lower than that for CPD in a model reaction, whereas 1,3-cycloheptadiene and 1,3-cyclooctadiene were found to be unable to

Synthesis of 1,2-divinylcyclopropanes by metal-catalyzed cyclopropanation of 1,3-dienes with cyclopropenes as vinyl carbene precursors

• Jesús González,
• Alba de la Fuente,
• María J. González,
• Laura Díez de Tejada,
• Luis A. López and
• Rubén Vicente

Beilstein J. Org. Chem. 2019, 15, 285–290, doi:10.3762/bjoc.15.25

• , the use of cyclopentadiene in the reaction with 1a and 1b enabled the preparation of divinylcyclopropanes 3d,e in good yields. Both catalysts provided similar yields, while complete endo selectivity was only reached with [Rh2(OAc)4]. Interestingly, the use of 1,3-cyclooctadiene led to the formation of

Nanoreactors for green catalysis

• M. Teresa De Martino,
• Loai K. E. A. Abdelmohsen,
• Floris P. J. T. Rutjes and
• Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

• reactions [95][97]. The first successful attempt was reported by Chung and Rhee, in which they showed the encapsulation of a bimetallic Pt–Pd catalyst in a highly branched PMAM-OH dendrimer corona [93]. These catalytic dendrimers were employed in partial hydrogenation of 1,3-cyclooctadiene into cyclooctene

Cyclodextrin nanosponge-sensitized enantiodifferentiating photoisomerization of cyclooctene and 1,3-cyclooctadiene

• Wenting Liang,
• Cheng Yang,
• Masaki Nishijima,
• Gaku Fukuhara,
• Tadashi Mori,
• Andrea Mele,
• Franca Castiglione,
• Fabrizio Caldera,
• Francesco Trotta and
• Yoshihisa Inoue

Beilstein J. Org. Chem. 2012, 8, 1305–1311, doi:10.3762/bjoc.8.149

• )-cyclooctene and (Z,Z)-1,3-cyclooctadiene were performed by using the pyromellitate-linked cyclodextrin network polymer, termed “cyclodextrin nanosponge (CDNS)”, as a supramolecular sensitizing host. The photochirogenic behavior of the nanosponges incorporating β- or γ-cyclodextrin was significantly different

• the photochirogenic reaction. Keywords: cyclodextrins; 1,3-cyclooctadiene; cyclooctene; nanosponge; photochirogenesis; photoisomerization; Introduction The precise control of chiral photoreactions, or photochirogenesis, is one of the most challenging topics in current photochemistry [1][2][3]. Weak

• photochirogenesis to use pyromellitate-linked polymeric β- and γ-CDs, termed “cyclodextrin nanosponges” (CDNSs) [25][26][27][28][29][30][31][32][33], as sensitizing hosts for the enantiodifferentiating photoisomerization of (Z)-cyclooctene (1Z) [34][35][36][37] and (Z,Z)-1,3-cyclooctadiene (2ZZ) [38][39][40