Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

Cerium-photocatalyzed aerobic oxidation of benzylic alcohols to aldehydes and ketones

• Girish Suresh Yedase,
• Sumit Kumar,
• Jessica Stahl,
• Burkhard König and
• Veera Reddy Yatham

Beilstein J. Org. Chem. 2021, 17, 1727–1732, doi:10.3762/bjoc.17.121

• 1ad and 1ae gave the ketones 2z, 2aa, 2ab, 2ac, 2ad, and 2ae in good yields. However, the primary aliphatic alcohol 3-phenylpropanol (1af) did not provide the desired aldehyde at all, and allylic alcohols such as geraniol (1ag) and cinnamyl alcohol (1ah) afforded the aldehydes 2ag and 2ah in very low

Copper catalysis with redox-active ligands

• Agnideep Das,
• Yufeng Ren,
• Cheriehan Hessin and
• Marine Desage-El Murr

Beilstein J. Org. Chem. 2020, 16, 858–870, doi:10.3762/bjoc.16.77

• alcohol to benzaldehyde, the authors also show that reaction with t-BuPhCuO.S.2 (5 mol %) could be efficiently extended to other substrates containing weak C–H bonds and acidic O–H bonds such as diphenylmethanol (PhBzOH), benzoin, and cinnamyl alcohol. However, alcohols with stronger C–H bonds

Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides

• Lingjun Xu,
• Shuwen Han,
• Linjie Yan,
• Haifeng Wang,
• Haihui Peng and
• Fener Chen

Beilstein J. Org. Chem. 2018, 14, 309–317, doi:10.3762/bjoc.14.19

• different alcohols (Table 3). Excellent yields with high enantioselectivities were obtained in all cases. The sterically more bulky 2-propanol worked well in this reaction. Allylic alcohol, benzyl alcohol and cinnamyl alcohol were also well compatible in this bifunctional organocatalysis conditions to

Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations

• Andrea Porcheddu,
• Evelina Colacino,
• Giancarlo Cravotto,
• Francesco Delogu and
• Lidia De Luca

Beilstein J. Org. Chem. 2017, 13, 2049–2055, doi:10.3762/bjoc.13.202

• oxidative procedure was also applied to allylic alcohol derivatives. Cinnamyl alcohol (1m) was transformed into the corresponding α,β-unsaturated aldehyde in an excellent yield (96%) and with the stereochemical retention of the double bond. Encouraged by these promising results, we attempted to oxidise

Continuous-flow processes for the catalytic partial hydrogenation reaction of alkynes

• Carmen Moreno-Marrodan,
• Francesca Liguori and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2017, 13, 734–754, doi:10.3762/bjoc.13.73

• and remarkable catalyst stability over a period of 24 h (Table 2, entries 17, 18). The heterogeneous hydrogenation of the parent alkyne substrate 3-phenyl-2-propyn-1-ol (12) is of interest because the corresponding alkene, the cinnamyl alcohol (12a + 12b), is used in the formulation of perfumes and

Selective synthesis of thioethers in the presence of a transition-metal-free solid Lewis acid

• Federica Santoro,
• Matteo Mariani,
• Federica Zaccheria,
• Rinaldo Psaro and
• Nicoletta Ravasio

Beilstein J. Org. Chem. 2016, 12, 2627–2635, doi:10.3762/bjoc.12.259

• reaction of optically active (R)-1-phenylethanol gave a completely racemic compound (Scheme 1). Unfortunately allylic alcohols gave unreproducible results. However, in the case of cinnamyl alcohol (1i) we could obtain a fairly good selectivity to the product of the thiol–ene reaction 3p (Scheme 2). The

• benzylmercaptan (2a) in the presence of SiAl 0.6. Reaction of cinnamyl alcohol 1i and benzylmercaptan (2a). Thioethers synthesis in solvent with different catalystsa. Synthesis of thioethers from different alcohols and thiols promoted by SiAl 0.6 without solventa. Supporting Information Supporting Information

A novel and practical asymmetric synthesis of dapoxetine hydrochloride

• Yijun Zhu,
• Zhenren Liu,
• Hongyan Li,
• Deyong Ye and
• Weicheng Zhou

Beilstein J. Org. Chem. 2015, 11, 2641–2645, doi:10.3762/bjoc.11.283

• encompass asymmetric dihydroxylation of trans-methyl cinnamate or cinnamyl alcohol [6], chiral azetidin-2,3-dione [7], asymmetric C–H amination reactions of a prochiral sulfamate [8], oxazaborolidine reduction of 3-chloropropiophenone or ketone [9], and an imidazolidin-2-one chiral auxiliary mediated

Phosphinate-containing heterocycles: A mini-review

• Olivier Berger and
• Jean-Luc Montchamp

Beilstein J. Org. Chem. 2014, 10, 732–740, doi:10.3762/bjoc.10.67

• 2 equivalents of cinnamyl alcohol 44 in the presence of 2 mol % of Pd/Xanthpos followed by an esterification using benzyl bromide. Ozonolysis, and reductive amination using excess benzylamine in the presence of sodium cyanoborohydride completed the synthesis. Phosphorines Two phosphorines 47a,b were

A new intermediate in the Prins reaction

• Shinichi Yamabe,
• Takeshi Fukuda and
• Shoko Yamazaki

Beilstein J. Org. Chem. 2013, 9, 476–485, doi:10.3762/bjoc.9.51

• TS1(Ph). A noticeable difference is found in the contrast of the stability order, ene-ol(Ph) > ether(Ph) versus ene-ol(Me) < ether(Me). The 3-phenyl-2-propenol (cinnamyl alcohol) is an allylic alcohol with the π conjugation of the phenyl ring and is thought to be the source of the stability of ene-ol

Inter- and intramolecular enantioselective carbolithiation reactions

• Asier Gómez-SanJuan,
• Nuria Sotomayor and
• Esther Lete

Beilstein J. Org. Chem. 2013, 9, 313–322, doi:10.3762/bjoc.9.36

• -disubstituted vinylcyclopropanes 8 in moderate to good enantiomeric excesses (Scheme 2b) [11]. More recently, enantioselective carbolithiation of cinnamyl alcohol has been reinvestigated by using (+)-sparteine surrogates, such as diamine L2 [12]. The best results are obtained by the treatment of cinnamyl

• fully developed. On the other hand, the high reactivity of the organolithiums requires the use of stoichiometric amounts of the chiral ligand. Intermolecular carbolithiation. Carbolithiation of cinnamyl and dienyl derivatives. Carbolithiation of cinnamyl alcohol. Carbolithiation of styrene derivatives

• alcohol (9) with the complex of butyllithium/diamine L2 in cumene at 0 °C, obtaining alcohol (R)-11 in 71% yield with 71% ee (Scheme 3). This is essentially opposite to the enantioselectivity obtained previously with (−)-sparteine L1 (82% yield, 83% ee in favor of (S)-11) [10]. Substituted styrene

A surprising new route to 4-nitro-3-phenylisoxazole

• Henning Hopf,
• Aboul-fetouh E. Mourad and
• Peter G. Jones

Beilstein J. Org. Chem. 2010, 6, No. 68, doi:10.3762/bjoc.6.68

• , Technische Universität Braunschweig, Postfach 3329, D-38023 Braunschweig, Germany 10.3762/bjoc.6.68 Abstract A one-pot synthesis of 4-nitro-3-phenylisoxazole has been carried out by treatment of cinnamyl alcohol dissolved in acetic acid with sodium nitrite; in addition, 4-phenyl-3-furoxanmethanol was

• obtained in 40% yield. Keywords: cinnamyl alcohol; furoxan derivatives; isoxazole derivatives; X-ray diffraction; Introduction The isoxazole ring system, which can be easily obtained by [3 + 2] cycloaddition of nitric oxides to alkynes, is of interest since it forms a part of various biodynamic agents

• phenylfuroxans 2 and 3 [10]. According to the original report, 4-phenyl-3-furoxanmethanol (2) was obtained as the sole product in 40% yield, by treatment of cinnamyl alcohol (1) dissolved in acetic acid with concentrated aqueous sodium nitrite at 70 °C (Scheme 1). Results and Discussion Application of this

A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis

• Magnus Rueping and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2010, 6, No. 6, doi:10.3762/bjoc.6.6

• . Other allylating reagents, such as β-methyl-, α,α-, and γ,γ-dimethylallyl alcohols or cinnamyl alcohol could also be used in this reaction. Additionally, high selectivity towards the linear allylated indoles was observed. Surprisingly, N-allylation did not occur. With L-tryptophan methyl ester (73) as

A short stereoselective synthesis of (+)-(6R,2′S)-cryptocaryalactone via ring- closing metathesis

• Palakodety Radha Krishna,
• Krishnarao Lopinti and
• K. L. N. Reddy

Beilstein J. Org. Chem. 2009, 5, No. 14, doi:10.3762/bjoc.5.14

• THF at 0 °C to give cinnamyl alcohol derivative 14 (87%, Scheme 3). Alcohol 14 was protected as its acetate under conventional reaction conditions. The PMB (p-methoxybenzyl protecting group) in compound 15 was selectively removed with DDQ in CH2Cl2/H2O (19:1) to afford homoallylic alcohol 16 (89