Synthesis of β-N-Phenylamino Alcohols and α-N-Phenylamino Acids via Reduction of the Adducts of Silyl Enol Ethers and Bis-silyl Ketene Acetals with Nitrosobenzene
Synthesis of 1,2-amino alcohols by decarboxylative coupling of amino acid derived α-amino radicals to carbonyl compounds <i>via</i> visible-light photocatalyst in water
coupling reaction of N-aryl amino acids with aldehydes or ketones for the synthesis of various 1,2-amino alcohols by using water as the solvent at room temperature is described. This protocol is characterised by broad substrate scopes, mild reaction conditions and amenability to gram-scale synthesis, which opens up a simple, mild but effective method to produce 1,2-amino alcohols from readily available
decarboxylative coupling of amino acids with aldehydes. A series of 1,2-amino alcohols are accessed in a transition-metal-free fashion under eco-friendly and redox-neutral conditions. The application of an urushiol-derived film in visible-lightphotoredoxcatalysis is also disclosed.
Gold-Catalyzed 1,2-Difunctionalizations of Aminoalkynes Using Only N- and O-Containing Oxidants
作者:Anupam Mukherjee、Ramesh B. Dateer、Rupsha Chaudhuri、Sabyasachi Bhunia、Somnath Narayan Karad、Rai-Shung Liu
DOI:10.1021/ja208150d
日期:2011.10.5
We report two viable routes for the 1,2difunctionalization of aminoalkynes using only oxidants. In the presence of a gold catalyst, nitrones enable the oxoamination of aminoalkynes 1 to form 2-aminoamides 2. With a suitable gold catalyst, nitrosobenzenes implement an alkyne/nitroso metathesis of the same substrates to give 2-oxoiminylamides 3. These two novel oxidations also provide 1,2-aminoalcohols with opposite regioselectivity via NaBH4 reduction in situ.
SASAKI, TADASHI;MORI, KOHKI;OHNO, MASATOMI, SYNTHESIS, BRD, 1985, N 3, 280-282