4391-81-5Relevant academic research and scientific papers
Combination of Enabling Technologies to Improve and Describe the Stereoselectivity of Wolff-Staudinger Cascade Reaction
Musio,Mariani,?liwiński,Kabeshov,Odajima,Ley
supporting information, p. 3515 - 3526 (2016/10/18)
A new, single-mode bench-top resonator was evaluated for the microwave-assisted flow generation of primary ketenes by thermal decomposition of α-diazoketones at high temperature. A number of amides and β-lactams were obtained by ketene generation in situ and reaction with amines and imines, respectively, in good to excellent yields. The preferential formation of trans-configured β-lactams was observed during the [2+2] Staudinger cycloaddition of a range of ketenes with different imines under controlled reaction conditions. Some insights into the mechanism of this reaction at high temperature are reported, and a new web-based molecular viewer, which takes advantage from Augmented Reality (AR) technology, is also described for a faster interpretation of computed data.
Diastereoselective Synthesis of syn-β-Lactams Using Rh-Catalyzed Reductive Mannich-Type Reaction of α,β-Unsaturated Esters
Isoda, Motoyuki,Sato, Kazuyuki,Funakoshi, Masato,Omura, Keiko,Tarui, Atsushi,Omote, Masaaki,Ando, Akira
, p. 8398 - 8405 (2015/09/01)
The combination of Et2Zn and RhCl(PPh3)3 led to the facile generation of a rhodium-hydride complex (Rh-H) that catalyzed the 1,4-reduction of α,β-unsaturated esters. The resulting rhodium enolate performed as a Reformatsky-type reagent and reacted with various imines to give syn-β-lactams in good to excellent yields with high diastereoselectivity.
Reductive Reformatsky-Honda reaction of α,β-unsaturated esters: Facile formation of 1,3-dicarbonyl compounds and β-hydroxy esters
Sato, Kazuyuki,Isoda, Motoyuki,Ohata, Shizuka,Morita, Shuhei,Tarui, Atsushi,Omote, Masaaki,Kumadaki, Itsumaro,Ando, Akira
supporting information; experimental part, p. 510 - 514 (2012/04/23)
The reaction of tris(triphenylphosphine)rhodium chloride [RhCl(PPh 3)3] with diethylzinc (Et2Zn) easily afforded a rhodium-hydride complex that effects the 1,4-reduction of α,β- unsaturated esters to give rhodium enolates. Formation of the rhodium enolate is followed by transmetalation with the zinc species to give a Reformatsky-type reagent, and this reacts with various acid chlorides at the α-position to give β-keto esters. The Reformatsky-type reagent also reacts with various electrophiles such as aldehydes, ketones and acid anhydrides to give the corresponding products in which the electrophiles were introduced reductively at the α-position of α,β-unsaturated esters. Copyright
Aldehydes vs aldimines. Unprecedented aldimine-selective nucleophilic additions in the coexistence of aldehydes using a lanthanide salt as a Lewis acid catalyst
Kobayashi, Shu,Nagayama, Satoshi
, p. 10049 - 10053 (2007/10/03)
It is well-recognized that aldimines are less reactive than aldehydes toward nucleophilic additions. In this paper, an unprecedented change in the reactivity is described: preferential reactions of aldimines over aldehydes in nucleophilic additions using
MILD AND CONVENIENT ONE-POT SYNTHESIS OF β-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES
Cinquini, Mauro,Cozzi, Franco,Cozzi, Pier Giorgio,Consolandi, Emanuela
, p. 8767 - 8774 (2007/10/02)
Treatment of 2-pyridylthioesters with triethylamine in the presence of titanium tetrachloride affords titanium enolates that add to imines to give β-lactams in fair to excellent yields with moderate to good stereoselectivity.
Highly enantioselective and diastereoselective synthesis of β-amino acid esters and β-lactams from achiral esters and imines
Corey,Decicco, Carl P.,Newbold, Ronald C.
, p. 5287 - 5290 (2007/10/02)
The reaction of S-tert-butyl thiopropionate with a number of N-benzyl or N-allyl aldimines (4) as promoted by the chiral diazaborolidine 1 and triethylamine afforded the β-amino acid esters 5 with high diastereoselectivity and enantioselectivity, providin
