60340-28-5Relevant academic research and scientific papers
Highly Chemoselective Allylation of Aldehydes in the Presence of Ketones
Kim, Sunggak,Kim, Sung Hoon
, p. 3723 - 3724 (1995)
Highly chemoselective allylationn of aldehydes in the presence of ketones has been achieved by preferential in situ conversion of aldehydes into 1-silyloxysulfonium salts and subsequent displacement with ally;tributyltin.
Unexpected Outcome of NbCl5-Promoted Sakurai Reaction: Mechanistic Implications Relevant to C4H7+ Species
Maeta, Hideki,Nagasawa, Tetsuya,Handa, Yasuhiko,Takei, Toru,Osamura, Yoshihiro,Suzuki, Keisuke
, p. 899 - 902 (1995)
Use of NbCl5 in the Sakurai reaction gave an unexpected outcome.Allylsilane reacted with aldehyde in 2:1-stoichiometry with concomitant formation of a cyclopropane ring.Mechanistic implications of this anomalous reaction related to C4H7+ specie
Total Synthesis of Diocollettines A via an Acid-Promoted Oxa-Michael-Aldol-Acetalization Cascade
Kawamoto, Misaki,Sato, Shuntaro,Enomoto, Masaru,Ogura, Yusuke,Kuwahara, Shigefumi
, p. 10099 - 10101 (2019)
A diastereo- and enantioselective total synthesis of diocollettines A with an unusual oxygen-containing tricyclic ring system has been achieved in 63% overall yield from commercially available 3-phenylpropanal via four steps. The key feature of the presen
Novel Lewis acid promoted reactions of allylsilane bearing bulky silyl substituents and aldehydes
Akiyama, Takahiko,Nakano, Michiko,Kanatani, Jun-Ya,Ozaki, Shoichiro
, p. 385 - 386 (1997)
Reported herein are two novel modes of reactions that were mediated by the proper choice of Lewis acid. Thus, by the influence of SnCl4, allyl-t-butyldimethylsilane reacted with aldehyde in 2:1 stoichiometry to afford a ketone derivative. In co
A Grignard-Type Addition of Allyl Unit to Carbonyl Compounds Containing a Carboxyl Group by Using BiCl3-Zn(0)-Allyl Bromide
Wada, Makoto,Honna, Munckazu,Kuramoto, Yoshihiro,Miyoshi, Norikazu
, p. 2265 - 2267 (1997)
In the presence of BiCl3-Zn(0), nearly equimolar amounts of allyl bromide reacted with carbonyl compounds containing a carboxyl group to afford the corresponding homoallylic alcohols having a carboxyl group or the intramolecular dehydrated lact
Racemization of homoallyl alcohols via an allyl-transfer reaction
Hussain, Iqbal,Komasaka, Tatsuhiko,Ohga, Masanori,Nokami, Junzo
, p. 640 - 642 (2002)
Acid-catalyzed asymmetric allylation of 3-phenylpropanal 2a via an allyl-transfer reaction from a chiral allyl donor, (1R,2S,5R)-1-allylmenthol, gave (R)-1-phenylhex-5-en-3-ol 3b enantioselectively. The optical yield (ee) of (R)-3b, however, decreased with increasing chemical yield, and the chemical yield increased with increasing reaction time. The racemization takes place via an acid-catalyzed allyl-transfer reaction from (R)-3b to 2a.
Cr(salen)-catalyzed asymmetric addition of allylstannane to aldehydes
Shimada, Yuya,Katsuki, Tsutomu
, p. 786 - 787 (2005)
Cr(salen) complex 3 was found to be an efficient catalyst for asymmetric addition of allyltributylstannane to non-branched aliphatic aldehydes, giving the corresponding homoallylic alcohols in a highly enantioselective manner. For example, its addition to
A Change from Kinetic to Thermodynamic Control Enables trans-Selective Stereochemical Editing of Vicinal Diols
Gu, Xin,Wendlandt, Alison E.,Zhang, Yu-An
supporting information, p. 599 - 605 (2022/01/03)
Here, we report the selective, catalytic isomerization of cis-1,2-diols to trans-diequatorial-1,2-diols. The method employs triphenylsilanethiol (Ph3SiSH) as a catalyst and proceeds under mild conditions in the presence of a photoredox catalyst and under
Visible Light-Promoted Recyclable Carbon Nitride-Catalyzed Dioxygenation of β,γ-Unsaturated Oximes
Fu, Xiao-Yang,Si, Ya-Feng,Qiao, Li-Peng,Zhao, Yu-Fen,Chen, Xiao-Lan,Yu, Bing
supporting information, p. 574 - 580 (2021/11/13)
A visible-light-induced dioxygenation of β,γ-unsaturated oximes for the synthesis of diverse useful isoxazolines bearing a hydroxyl moiety was developed by employing graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst under an air atmosphere. Noted that, the eminent advantages of this metal-free protocol include step economy, easy operation, a recyclable photocatalyst, external reductant-/oxidant-free and mild reaction conditions. Additionally, mechanistic studies indicated hydroxyl radical was generated under the photocatalysis of g-C3N4.
Nitrogen-Doped Carbon-Incarcerated Zinc Electrodes as Heterogeneous Catalysts for Electrochemical Allylation of Carbonyl Compounds
Masuda, Ryusuke,Yasukawa, Tomohiro,Yamashita, Yasuhiro,Kobayashi, Shū
, p. 3453 - 3460 (2022/02/23)
Electrochemical allylation reactions of carbonyl compounds using cathodes prepared from nitrogen-doped carbon (NDC)-incarcerated zinc catalysts have been developed. A range of aldehydes and ketones afforded the desired allylic alcohols in high yields with 10 mol % zinc leaching, and the heterogeneous nature of the active species was suggested. Compared with bulk zinc electrodes, NDC-stabilized zinc nanoparticle species were compatible with a broader range of heteroaromatic substrates and enabled the use of an undivided cell.
