736172-42-2Relevant academic research and scientific papers
Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols
Jiang, Yao,Schaus, Scott E.
, p. 1544 - 1548 (2017/02/05)
Chiral biphenols catalyze the asymmetric Petasis borono-Mannich allylation of aldehydes and amines through the use of a bench-stable allyldioxaborolane. The reaction proceeds via a two-step, one-pot process and requires 2–8 mole % of 3,3′-Ph2-BINOL as the optimal catalyst. Under microwave heating the reaction affords chiral homoallylic amines in excellent yields (up to 99 %) and high enantioselectivies (er up to 99:1). The catalytic reaction is a true multicomponent condensation reaction whereas both the aldehyde and the amine can possess a wide range of structural and electronic properties. Use of crotyldioxaborolane in the reaction results in stereodivergent products with anti- and syn-diastereomers both in good diastereoselectivities and enantioselectivities from the corresponding E- and Z-borolane stereoisomers.
Indium-assisted aluminium-based stereoselective allylation of prostereogenic α,α-disubstituted cycloalkanones and imines
Reddy, Chennakesava,Babu, Srinivasarao Arulananda,Aslam, Nayyar Ahmad
, p. 40199 - 40213 (2014/12/10)
The use of a catalytic amount of InCl3in combination with Al0for the allylation of a variety of prostereogenic α,α-disubstituted (hindered) cycloalkanones, 1,2-dione-based systems and various imino systems (CN functional groups) is reported. The stereoselective InCl3-catalyzed Al-based allylation of various 2-substituted-2-carbethoxycycloalkanones gave the corresponding products with moderate to excellent diastereoselectivity. The allylation and propargylation of imines including α-imino esters using a catalytic amount of InCl3in combination with Al0gave the corresponding allylated and propargylated compounds in moderate to good yields. If γ-substituted allylic halides were added to imino compounds, low to very good diastereoselectivity was obtained. The allylation of chiral N-tert-butylsulfinyl imine systems gave the corresponding products in moderate yields with good to excellent diastereoselectivity. This journal is
Diene-ligated iridium catalyst for allylation reactions of ketones and imines
Barker, Timothy J.,Jarvo, Elizabeth R.
supporting information; experimental part, p. 1047 - 1049 (2009/08/15)
[Ir(cod)CI]2 is a highly reactive catalyst for allylation reactions of ketones using allylboronic ester. Mechanistic experiments are consistent with formation of a nucleophilic allyliridium(1) complex that is activated by the diene ligand towar
Palladium-catalyzed, one-pot, three-component synthesis of homoallylic amines from aldehydes, anisidine, and allyl trifluoroacetate
Grote, Robin E.,Jarvo, Elizabeth R.
supporting information; experimental part, p. 485 - 488 (2009/07/18)
(Chemical Equation Presented) An allylation reaction that generates homoallylic amines using allyl trifluoroacetate as a nucleophilic allylmetal precursor is reported. A palladium complex catalyzes two transformations in one pot: formation of allylsilane
