Amines as key building blocks in Pd-assisted multicomponent processes

• Didier Bouyssi,
• Nuno Monteiro and
• Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

• cyclofunctionalization of the allyl moiety by carbopalladation/reductive elimination [22]. It is interesting to note that 3-sulfonylpyrolidin-2-ones (γ-lactams) 48 may also be accessed in high yield as single trans-diastereomers upon simple treatment of N-allyl- or N-methylpyrrolidines with 2-mercaptobenzoic acid in

• boiling MeCN. Acid-promoted formation of a ring-opened iminium salt intermediate 47, followed by hydrolysis and subsequent intramolecular attack of the released secondary amine onto the ester group, would account for the formation of the γ-lactams [23]. This unexpected transformation was observed during

Tandem catalysis of ring-closing metathesis/atom transfer radical reactions with homobimetallic ruthenium–arene complexes

• Yannick Borguet,
• Xavier Sauvage,
• Guillermo Zaragoza,
• Albert Demonceau and
• Lionel Delaude

Beilstein J. Org. Chem. 2010, 6, 1167–1173, doi:10.3762/bjoc.6.133

• generate active species in situ. The two catalytic processes were first carried out independently in a case study before the whole sequence was optimized and applied to the synthesis of several polyhalogenated bicyclic γ-lactams and lactones from α,ω-diene substrates bearing trihaloacetamide or

• reactions with homobimetallic ruthenium–indenylidene complex 1 to generate active species in situ. The two catalytic processes were first carried out independently in a case study before the whole sequence was optimized and applied to the synthesis of several polyhalogenated bicyclic γ-lactams and lactones

Synthesis of fluorinated δ-lactams via cycloisomerization of gem-difluoropropargyl amides

• Satoru Arimitsu and
• Gerald B. Hammond

Beilstein J. Org. Chem. 2010, 6, No. 48, doi:10.3762/bjoc.6.48

• ; cycloisomerization; difluoropropargyl; enyne; ring-closing metathesis; Introduction It has been estimated that as many as 25% of all synthetic pharmaceutical drugs contain an amide bond [1]. Commonly, β- and γ-lactams are present in many natural products and pharmaceuticals, and the introduction of a gem

• ][6][7][8]. Our group’s entry in this arena started as a collaboration with Professor Fustero and resulted in the syntheses of fluorinated β- and γ-lactams [9][10][11][12][13]. This sparked our interest in the synthesis of larger-ring lactams, with six to eight members, because nitrogen-containing

Palladium- catalyzed cross coupling reactions of 4-bromo- 6H-1,2-oxazines

• Reinhold Zimmer,
• Elmar Schmidt,
• Michal Andrä,
• Marcel-Antoine Duhs,
• Igor Linder and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2009, 5, No. 44, doi:10.3762/bjoc.5.44

• derivatives constitute a versatile class of N,O heterocycles [1][2][3][4][5][6][7][8][9][10][11][12][13]. Considerable attention has been paid to 6H-1,2-oxazines 1 bearing a C-4,C-5-double bond [14][15][16][17][18], which are useful intermediates in the synthesis of γ-lactams [19], γ-amino acids [20], amino