Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines

• Ashley N. Jarvis,
• Andrew B. McLaren,
• Helen M. I. Osborn and
• Joseph Sweeney

Beilstein J. Org. Chem. 2013, 9, 852–859, doi:10.3762/bjoc.9.98

• -sulfonylation in aziridine chemistry, due to the ability of the group to activate the ring and the relative ease of its removal at the conclusion of a synthetic manipulation. We report here in full [30] the results of our studies on the synthesis of N-Dpp vinyl azidirines, and selected ring-opening reactions of

Exploring chemical diversity via a modular reaction pairing strategy

• Joanna K. Loh,
• Sun Young Yoon,
• Thiwanka B. Samarakoon,
• Alan Rolfe,
• Patrick Porubsky,
• Benjamin Neuenswander,
• Gerald H. Lushington and
• Paul R. Hanson

Beilstein J. Org. Chem. 2012, 8, 1293–1302, doi:10.3762/bjoc.8.147

• nucleophilic aromatic substitution (SNAr) diversification pathway is reported. Eight benzofused sultam cores were generated by means of a sulfonylation/SNAr/Mitsunobu reaction pairing protocol, and subsequently diversified by intermolecular SNAr with ten chiral, non-racemic amine/amino alcohol building blocks

• , namely sulfonylation, Mitsunobu alkylation and SNAr, which when combined in different sequences or with different coupling reagents, give access to skeletally diverse sultams, including the title compounds and the 8-membered bridged, benzofused sultams [32]. Building on this strategy, we herein report

• on multigram scale through the use of three efficient steps, namely sulfonylation, Mitsunobu alkylation and SNAr, to generate both stereoisomers of each core [37] (Scheme 2). The bridged benzofused sultam scaffolds were prepared by a sulfonylation intramolecular SNAr protocol, reported previously [32

An intramolecular inverse electron demand Diels–Alder approach to annulated α-carbolines

• Zhiyuan Ma,
• Feng Ni,
• Grace H. C. Woo,
• Sie-Mun Lo,
• Philip M. Roveto,
• Scott E. Schaus and
• John K. Snyder

Beilstein J. Org. Chem. 2012, 8, 829–840, doi:10.3762/bjoc.8.93

• condensation with different solvents was needed to optimize the triazine formation. Sulfonylation of the indole nitrogen also proceeded routinely to give triazine 8a (R1 = H, R2 = p-Tol), and served two purposes. As noted, the reduction of electron donation from this nitrogen into the triazine ring was thought

• to be important for the subsequent cycloaddition to proceed, as was shown to be correct in later studies. Furthermore, sulfonylation greatly improved the solubility of the triazines 8 in organic solvents in comparison to 9, which showed only limited solubility in dichloromethane, chloroform, THF

Anion receptors containing thiazine-1,1-dioxide heterocycles as hydrogen bond donors

• Hong-Bo Wang,
• James A. Wisner and
• Michael C. Jennings

Beilstein J. Org. Chem. 2010, 6, No. 50, doi:10.3762/bjoc.6.50

• typically been realized synthetically by sulfonylation of an amine to form a sulfonamide product. This approach is somewhat limited, from a design perspective, in that the majority of examples to date consist of sulfonamides derived from a few commercially available starting materials such as

Enantiospecific synthesis of [2.2]paracyclophane- 4-thiol and derivatives

• Gareth J. Rowlands and
• Richard J. Seacome

Beilstein J. Org. Chem. 2009, 5, No. 9, doi:10.3762/bjoc.5.9

• ]paracyclophane compounds; aryl sulfonylation and the related sulfenylation facilitates the synthesis of sulfonic acids, sulfonamides and protected thiols [24][25][26] whilst directed metallation has allowed the formation of various sulfides [27][28][29][30]. Very few methodologies allow the synthesis of simple