1620-61-7Relevant articles and documents
Domino Synthesis of α,β-Unsaturated γ-Lactams by Stereoselective Amination of α-Tertiary Allylic Alcohols
Xie, Jianing,Xue, Sijing,Escudero-Adán, Eduardo C.,Kleij, Arjan W.
, p. 16727 - 16731 (2018/11/23)
Tertiary allylic alcohols equipped with a carboxyl group can be smoothly aminated under ambient conditions by a conceptually new and stereoselective protocol under palladium catalysis. The in situ formed Z-configured γ-amino acid cyclizes to afford an α,β-unsaturated γ-lactam, releasing water as the only byproduct. This practical catalytic transformation highlights the use of a carboxyl group acting as an activating and stereodirecting functional group to provide a wide series of pharma-relevant building blocks. Various control reactions support the crucial role of the carboxyl group in the substrate to mediate these transformations.
Enantioselective alkenylation and phenylation catalyzed by a chiral CuF complex
Tomita, Daisuke,Wada, Reiko,Kanai, Motomu,Shibasaki, Masakatsu
, p. 4138 - 4139 (2007/10/03)
A new method for CuF-catalyzed alkenylation and phenylation of aldehydes and an activated ketone using air- and moisture-stable alkenylsilanes and phenylsilane as a nucleophile is described. This methodology was extended to highly enantioselective catalytic alkenylation and phenylation using DTBM-SEGPHOS as a chiral ligand. Substrate generality is broad, and an alkenylsilane with a long alkyl chain and an internal alkenylsilane can be also used as a nucleophile. The key to success partly involves the accelerated regeneration of reactive alkenylcopper and phenylcopper through transmetalation from the silylated nucleophiles, and stabilization of the reactive copper reagents, both of which are effected by the diphosphine ligands. Copyright
