140226-81-9Relevant academic research and scientific papers
Synthesis of functionalized epoxides by copper-catalyzed alkylative epoxidation of allylic alcohols with alkyl nitriles
Bunescu, Ala,Wang, Qian,Zhu, Jieping
supporting information, p. 1890 - 1893 (2015/04/27)
A copper-catalyzed oxyalkylation of allylic alcohols using nonactivated alkyl nitriles as reaction partners was developed. A sequence involving generation of an alkyl nitrile radical followed by its addition to a double bond and a copper-mediated formation of C(sp3)-O bond was proposed to account for the reaction outcome. The protocol provided an efficient route to functionalized tri- and tetrasubstituted epoxides via formation of a C(sp3)-C(sp3) and a C(sp3)-O bond with moderate to excellent diastereoselectivity.
Nonenzymatic kinetic resolution of α-aryl substituted allylic alcohols catalyzed by acyl transfer catalyst Np-PIQ
Jiang, Shan-Shan,Gu, Bo-Qi,Zhu, Ming-Yu,Yu, Xingxin,Deng, Wei-Ping
, p. 1187 - 1191 (2015/02/19)
Chiral α-aryl substituted allylic alcohols are important versatile synthetic intermediates. We report here an effective nonenzymatic kinetic resolution of racemic α-aryl substituted allylic alcohols by introducing different aryl groups with acyl transfer
Non-enzymatic acylative kinetic resolution of primary allylic amines
Kolleth, Amandine,Cattoen, Martin,Arseniyadis, Stellios,Cossy, Janine
supporting information, p. 9338 - 9340 (2013/10/01)
A non-enzymatic acetyl transfer-based kinetic resolution of primary allylic amines is reported. The process involves the use of (1S,2S)-1 in conjunction with a supported ammonium salt and affords the corresponding enantio-enriched N-acetylated allylic ami
One-pot synthesis of α,β-epoxy ketones by palladium-catalyzed epoxidation-oxidation of terminal allylic alcohols
Singh, Fateh V.,Pena, Jesus M.,Stefani, Hélio A.
experimental part, p. 1671 - 1673 (2010/05/19)
Described herein is a one-pot synthesis of α,β-epoxy ketones using a palladium-catalyzed epoxidation-oxidation sequence. Functionalized terminal allylic alcohols are treated with m-CPBA under mild reaction conditions to obtain the α,β-epoxy ketones. The m
Aziridination of 2- and 3-phenyl-substituted allylic alcohols with 3-acetoxyaminoquinazolinones: Probing the nature of the transition state from the diastereoselectivity of aziridination
Atkinson, Robert S.,Ulukanli, Sabri,Williams, Paul J.
, p. 2121 - 2128 (2007/10/03)
Aziridination of phenyl-substituted allylic alcohol 10 with 3-acetoxyaminoquinazolinone 3 (Q'NHOAc) and with 22 (Q2NHOAc) has been studied. The diastereoselectivity of these reactions is markedly changed by carrying them out in the presence of aqueous sodium hydrogen carbonate solution and under these conditions aziridinations of 10 and of its ester analogue 5 with Q2NHOAc give the same magnitude and sense of diastereoselectivity (with Ph=CO2Me). An explanation for these changes in diastereoselectivity is offered based upon differences in the nature of the hydrogen bonding in the transition states for aziridination of 10 with and without the presence of acetic acid.
A Convergent Method for the Stereoselective Synthesis of Trisubstituted Alkenes
Martin, Stephen F.,Daniel, Dilon,Cherney, Robert J.,Liras, Spiros
, p. 2523 - 2525 (2007/10/02)
A method for the stereoselective, convergent synthesis of trisubstituted alkenes has been developed.The procedure features the synthesis of allylic alcohols 9 by coupling an aldehyde with a vinyl organometallic reagent.Treatment of 9 with carbon disulfide
