13140-15-3Relevant articles and documents
The Synthesis of Butenamides and Thiobutenamide by an Organosamarium Reagent
Yu, Mingxin,Zhang, Yongmin,Qian, Cangtao
, p. 256 - 257 (1998)
An organosamarium reagent reacts with isocyanates (or isothiocyanate) to afford butenamides (or thiobutenamide) in THF.
Dehydrogenative Allylic Aminations of But-3-enoic Acid Derivatives
Diamante, Daria,Gabrieli, Sara,Benincori, Tiziana,Broggini, Gianluigi,Oble, Julie,Poli, Giovanni
, p. 3400 - 3412 (2016)
Two complementary Pd-catalyzed protocols enabling the γ-selective intermolecular allylic amination of but-3-enoic acid derivatives are reported. These transformations can be successfully achieved via either a direct Pd(II)-catalyzed protocol or by way of a one-pot Pd(II)/Pd(0)-catalyzed sequence, depending on the nature of the nitrogen nucleophile used.
Palladium-catalyzed tandem bis-allylation of isocyanates
Solin, Niclas,Narayan, Sanjay,Szabo, Kalman J.
, p. 909 - 912 (2001)
matrix presented A tandem bis-allylation of p-toluenesulfonyl isocyanate can be achieved by palladium-catalyzed three-component coupling reaction with allylstannanes and allyl chlorides. A high level of regioselectivity can be obtained by the appropriate choice of the allylic substituents. The reaction mechanism and the regiochemistry of the reaction can be explained by formation of an amphoteric bis-allylpalladium intermediate. This bis-allylpalladium intermediate undergoes an initial electrophilic attack on one of the allyl moieties followed by a nucleophilic attack on the other.
Electophilic activation of carbon dioxide. Preparation of vinylacetic acid from CO2 and allyltrimethylsilane
Vol'pin, M. E.,Sigan, A. L.,Solomovich, E. V.
, p. 1929 - 1930 (1993)
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Photocatalyzed Triplet Sensitization of Oximes Using Visible Light Provides a Route to Nonclassical Beckmann Rearrangement Products
Zhang, Xiao,Rovis, Tomislav
supporting information, p. 21211 - 21217 (2021/12/27)
Oximes are valuable synthetic intermediates for the preparation of a variety of functional groups. To date, the stereoselective synthesis of oximes remains a major challenge, as most current synthetic methods either provide mixtures of E and Z isomers or furnish the thermodynamically preferred E isomer. Herein we report a mild and general method to achieve Z isomers of aryl oximes by photoisomerization of oximes via visible-light-mediated energy transfer (EnT) catalysis. Facile access to (Z)-oximes provides opportunities to achieve regio- and chemoselectivity complementary to those of widely used transformations employing oxime starting materials. We show an enhanced one-pot protocol for photocatalyzed oxime isomerization and subsequent Beckmann rearrangement that enables novel reactivity with alkyl groups migrating preferentially over aryl groups, reversing the regioselectivity of the traditional Beckmann reaction. Chemodivergent N- or O- cyclizations of alkenyl oximes are also demonstrated, leading to nitrones or cyclic oxime ethers, respectively.
A practical copper-catalyzed approach to β-lactams: via radical carboamination of alkenyl carbonyl compounds
Shi, Peng,Wang, Jie,Gan, Zixu,Zhang, Jingyu,Zeng, Runsheng,Zhao, Yingsheng
supporting information, p. 10523 - 10526 (2019/09/06)
Functionalized β-lactams are highly important motifs in synthetic chemistry. We report an efficient and novel approach to the synthesis of β-lactams via a copper(i)-catalyzed cascade process involving C(benzyl)-H radical abstraction, intermolecular alkene addition, and intramolecular amination reaction. Variously substituted alkenes were synthesized from vinylacetic acid, leading to the corresponding β-lactams in moderate to good yields. Preliminary studies indicate that the reaction undergoes a free radical mechanism via a Cu(i)/Cu(ii)/Cu(iii) catalytic cycle.
