24948-31-0Relevant academic research and scientific papers
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.
Stereodefined homopropargyl amines by tandem nucleophilic addition/fragmentation of dihydropyridone triflates
Tummatorn, Jumreang,Dudley, Gregory B.
supporting information; experimental part, p. 158 - 160 (2011/03/20)
Dihydropyridone (DHPD) triflates undergo nucleophile-triggered fragmentation to provide homopropargyl amine derivatives, the stereochemistry of which is defined by starting from readily available β-amino esters.
An efficient and mild bismuth triflate-catalysed three-component Mannich-type reaction
Ollevier, Thierry,Nadeau, Etienne
, p. 3126 - 3134 (2008/04/01)
In the presence of a catalytic amount of Bi(OTf)3·4H 2O, aldehydes together with amines react with silyl enolates to afford the corresponding Mannich-type adducts smoothly. A wide variety of silyl enolates derived from ketones, as well as esters and thioesters, react rapidly to afford the β-amino ketones or the β-amino esters in high yields (up to 94%). The Royal Society of Chemistry.
Synthesis of β-amino esters by bismuth triflate catalyzed three-component Mannich-type reaction
Ollevier, Thierry,Nadeau, Etienne
, p. 219 - 222 (2007/10/03)
We have developed an efficient, bismuth-catalyzed, Mannich-type three-component reaction by combining the corresponding aldehyde, amine, and silyl ketene acetal. The reaction proceeds rapidly and affords the corresponding β-amino esters in high yields (up
One-pot synthesis of β-lactams from aldimines and ketene silyl acetals by tandem lewis base-catalyzed Mannich-type addition and cyclization
Takahashi, Eiki,Fujisawa, Hidehiko,Yanai, Toshiharu,Mukaiyama, Teruaki
, p. 216 - 217 (2007/10/03)
An efficient method for one-pot synthesis of β-lactams from aldimines and ketene silyl acetals by tandem Lewis base-catalyzed Mannich-type addition and cyclization, namely reaction of benzylideneanilines and trimethylsilyl enolates derived from esters or thioesters was established by using a Lewis base catalyst such as lithium acetate, N-lithio-2-pyrrolidone, potassium salt of phthalimide or lithium methoxide in DMF at room temperature to afford the corresponding β-lactams in good to high yields with moderate trans-selectivities. Copyright
Solvent-free imino-aldol three-component couplings on a conveniently-prepared and reusable phosphoric acid-silica gel support
Lock, Sandra,Miyoshi, Norikazu,Wada, Makoto
, p. 1308 - 1309 (2007/10/03)
A new solvent-free procedure for the synthesis of β-amino carbonyl compounds in generally moderate to excellent yields has been developed. Three-component Mannich-type couplings between aldehydes (aromatic, aliphatic, alicyclic, and heterocyclic), aromatic amines and silyl enol equivalents proceeded smoothly on a conveniently prepared and reusable phosphoric acid-silica gel solid support.
TTMPP catalyzed one-pot silyl ketene acetal-imine condensation route to β-lactams
Matsukawa, Satoru,Obu, Kayoko
, p. 1626 - 1627 (2007/10/03)
Highly nucleophilic phosphine, tris(2,4,6-trimethoxy phenyl) phosphine (TTMPP) catalyzes a unique one-pot cyclization reaction between silyl ketene acetal and aldimine, resulting in β-lactam. Copyright
Rhodium-catalyzed approach to Mannich-type products using aldimine, α,β-unsaturated ester, and hydrosilane
Muraoka, Takako,Kamiya, Shin-Ichi,Matsuda, Isamu,Itoh, Kenji
, p. 1284 - 1285 (2007/10/03)
A rhodium-catalyzed method for the synthesis of β-amino esters was accomplished in a one-pot procedure from aldimine, α,β-unsaturated ester and hydrosilane.
Asymmetric 13-dipolar cycloaddition of nitrones with ketene acetals catalyzed by chiral oxazaborolidines
Seerden, Jean-Paul G.,Schotte Op Reimer, Anita W. A.,Scheeren, Hans W.
, p. 4419 - 4422 (2007/10/02)
Asymmetric 1,3-dipolar cycloaddition of nitrones with ketene acetals is strongly catalyzed by chiral oxazaborolidines derived from N-tosyl-L-α-amino acids. The 5,5-dialkoxyisoxazolidines are obtained regioselectivity in high yield with high stereoselectiv
Synthesis in dry media coupled with microwave irradiation: Application to the preparation of β-aminoesters and β-lactams via silyl ketene acetals and aldimines
Texier-Boullet, Francoise,Latouche, Regine,Hamelin, Jack
, p. 2123 - 2126 (2007/10/02)
According to the reaction conditions, silyl ketene acetals react with aldimines to give β-aminoesters (montmorillonite clay K10, or para-toluenesulfonic acid) or β-lactams (KF/18 crown-6) in a few minutes under microwave irradiation.
