Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid

• Emeline Benoit,
• Ahmed Fnaiche and
• Alexandre Gagnon

Beilstein J. Org. Chem. 2019, 15, 1162–1171, doi:10.3762/bjoc.15.113

• with hydrobromic acid and zinc bromide leads to 1-arylthiocyclobutenes 7 [13] and 2-alkyl-substituted cyclobutanones 8 [11][12], respectively. Treatment of 6 with hydrobromic acid and zinc bromide in the presence of a thiophenol provides the 1,1-di(arylthio)cyclobutane 9 which, upon reaction with

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

• % and 9% yields, respectively (Scheme 30) [273]. However, in order to perform the asymmetric oxidation of 3-substituted cyclobutanones 96a–f to the corresponding lactones 97a–f (Table 7) [274], it is necessary to employ chiral Brønsted acids [274][275][276][277], organocatalysts [278][279] or enzymes

Alkoxide-induced ring opening of bicyclic 2-vinylcyclobutanones: A convenient synthesis of 2-vinyl-substituted 3-cycloalkene-1-carboxylic acid esters

• Xiufang Ji,
• Zhiming Li,
• Quanrui Wang and
• Andreas Goeke

Beilstein J. Org. Chem. 2012, 8, 650–657, doi:10.3762/bjoc.8.72

• cyclobutanones 4 undergo stereoselective ring openings by the action of alkoxide ions (t-BuO− or MeO−) to produce novel vicinally disubstituted cycloalkene derivatives 5 and 6 in moderate to high yields. The ring cleavage usually occurs with complete regioselectivity. The accessibility of γ,δ-unsaturated ester

• or acid derivatives makes this transformation a good supplementary method for the well-established Johnson–Claisen rearrangement. Keywords: alkoxide; cyclobutanones; esters; fused ring systems; ring opening; Introduction A great variety of methods are available for the synthesis of cyclobutane

• . In particular, due to their facile accessibility [3][4][5][6][7][8] and expeditious ring transformations, the use of cyclobutanones as extremely versatile and useful starting materials or intermediates in the construction of carbon skeletons has flourished over the past three decades [9][10]. In

Recent advances in the gold-catalyzed additions to C–C multiple bonds

• He Huang,
• Yu Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103

Synthetic applications of gold-catalyzed ring expansions

• David Garayalde and
• Cristina Nevado

Beilstein J. Org. Chem. 2011, 7, 767–780, doi:10.3762/bjoc.7.87

• expansions involving oxygenated functions 1.1 Cyclopropanols and cyclobutanols Substituted cyclobutanones [13][14][15] and cyclopentanones [16][17][18] constitute valuable building blocks in organic synthesis due to their rich chemistry. In addition, they are common motifs in numerous natural products. Among

• 19 can be transformed into cyclobutanones 20 with absolute stereocontrol at the quaternary stereogenic center generated during the reaction by the use of a binuclear chiral gold-phosphine complex, as shown in Scheme 6 [22]. Bicyclic cyclopentanones can also be obtained in a related transformation