52922-10-8Relevant articles and documents
Chiral bronsted acid-catalyzed allylboration of aldehydes
Jain, Pankaj,Antilla, Jon C.
, p. 11884 - 11886 (2010)
The catalytic enantioselective allylation of aldehydes is a long-standing problem of considerable interest to the chemical community. We disclose a new high-yielding and highly enantioselective chiral Bronsted acid-catalyzed allylboration of aldehydes. Th
Enhancement of threo-Selectivity in the Reaction of But-2-enyl-lithium with Aldehydes via Allylic Boronate Complexes
Yamamoto, Yoshinori,Yatagai, Hidetaka,Maruyama, Kazuhiro
, p. 1072 - 1073 (1980)
The threo-selectivity of the reaction of but-2-enyl-lithium with aldehydes in the presence of certain trialkylboranes is enhanced; the corresponding allylic boronate complexes are presumably involved as intermediates.
Kinetic Resolution of α-Silyl-Substituted Allylboronate Esters via Chemo- and Stereoselective Allylboration of Aldehydes
Park, Jinyoung,Jung, Yongsuk,Kim, Jeongho,Lee, Eunsung,Lee, Sarah Yunmi,Cho, Seung Hwan
supporting information, p. 2371 - 2376 (2020/12/01)
We describe the kinetic resolution of α-silyl-substituted allylboronate esters via chiral phosphoric acid-catalyzed chemo-, diastereo- and enantioselective allylboration of aldehydes. This process provides two synthetically versatile enantioenriched compo
Photoredox Ni-Catalyzed Branch-Selective Reductive Coupling of Aldehydes with 1,3-Dienes
Chen, Jie,Gu, Zheng-Yang,Li, Wen-Duo,Li, Yan-Lin,Xia, Ji-Bao
, p. 1528 - 1534 (2020/02/04)
We report here a Ni-catalyzed reductive coupling of aldehydes with widely available 1,3-dienes under visible-light photoredox dual catalysis. The homoallyic alcohols are obtained in broad scope with complete branched regioselectivity. Hantzsch ester is used as the hydrogen radical source to oxidize low-valent nickel salt affording Ni-H species. Preliminary mechanistic studies indicate a successive single-electron transfer (SET) pathway and the generation of a key π-allylnickel intermediate via Ni-H insertion of 1,3-diene in this synergistic catalytic process.
Active bismuth mediated allylation of carbonyls/N-tosyl aldimines and propargylation of aldehydes in water
Sawkmie, Micky Lanster,Paul, Dipankar,Khatua, Snehadrinarayan,Chatterjee, Paresh Nath
, (2019/06/08)
Abstract: Active bismuth is synthesized by the chemical reduction of bismuth trichloride using freshly prepared sodium stannite solution as the reducing agent at room temperature. The as-synthesized active bismuth is applied as a reagent for the synthesis of homoallyl alcohol/homopropargyl alcohol from allyl bromide/propargyl bromide and carbonyl compounds in water at 50°C. The homoallyl amines are also synthesized from N-tosyl aldimines and allyl bromide using active bismuth reagent in good yields. No assistance of organic co-solvent, co-reagent, phase transfer catalyst or inert atmosphere is required for this reaction. The waste bismuth material obtained after the completion of the organic reaction can be reduced to active bismuth by sodium stannite solution and successfully reused for mediating the allylation of aldehydes. Graphical Abstract:: Synopsis Active bismuth mediated allylation/crotylation of aldehydes is developed in water to get homoallyl alcohols. The method is also applied for the allylation of N-tosyl aldimines and propargylation of aldehydes in water to achieve the homoallyl amines and homopropargyl alcohols, respectively. The reactions do not require the assistance of organic co-solvent, co-reagent, phase transfer catalyst or inert atmosphere.[Figure not available: see fulltext.].