Iron complexes of tetramine ligands catalyse allylic hydroxyamination via a nitroso–ene mechanism

• David Porter,
• Belinda M.-L. Poon and
• Peter J. Rutledge

Beilstein J. Org. Chem. 2015, 11, 2549–2556, doi:10.3762/bjoc.11.275

• situ along with chiral oxazolines [16][17], N-oxides [19] or amines [18][20][21] as ligands or organocatalysts. In these nitrosoaldol contexts, the chiral agents induce asymmetry by virtue of their influence over the enolate reaction partner. Achieving asymmetric induction in the nitroso–ene reaction

Palladium-catalysed cyclisation of alkenols: Synthesis of oxaheterocycles as core intermediates of natural compounds

• Miroslav Palík,
• Jozef Kožíšek,
• Peter Koóš and
• Tibor Gracza

Beilstein J. Org. Chem. 2014, 10, 2077–2086, doi:10.3762/bjoc.10.216

• 2 steps starting from the aldehyde 31 using the Yamamoto’s [33] sequential O-nitrosoaldol and Grignard addition process using different reagents (Scheme 4). Thus, L-proline-catalysed oxidation of 31 with 2-nitrosotoluene gave the optically pure O-selective nitrosoaldol product 32, which underwent a

Enantioselective total synthesis of (R)-(−)-complanine

• Krystal A. D. Kamanos and
• Jonathan M. Withey

Beilstein J. Org. Chem. 2012, 8, 1695–1699, doi:10.3762/bjoc.8.192

• complanata, and known to be a causative agent in inflammation. An organocatalytic, asymmetric oxyamination of a homoconjugated all-Z-dienal intermediate provides versatile and efficient access to the natural product. Keywords: complanine; enantioselective synthesis; marine fireworm; nitrosoaldol

• asymmetric organocatalytic O-nitrosoaldol reaction as the source of chirality, with accompanying amination of the aldehyde functional group resulting in a concise and efficient synthesis. Results and Discussion Herein we report the concise and efficient synthesis of (R)-(−)-complanine, via a highly effective

• organocatalytic O-nitrosoaldol as the key step. A retrosynthetic analysis for complanine is depicted in Scheme 1. The synthesis was initiated by preparation of homoconjugated all-Z-diene 1 (Scheme 2). Sequential olefin preparation by using Wittig chemistry, or selective polyyne reduction represent two traditional