34094-39-8Relevant articles and documents
Enantioselective Synthesis of Cyclopropanone Equivalents and Application to the Formation of Chiral β-Lactams
Jang, Yujin,Johnson, J. Drake,Jung, Myunggi,Lindsay, Vincent N. G.,Poteat, Christopher M.,Williams, Rachel G.
supporting information, p. 18655 - 18661 (2020/08/21)
Cyclopropanone derivatives have long been considered unsustainable synthetic intermediates because of their extreme strain and kinetic instability. Reported here is the enantioselective synthesis of 1-sulfonylcyclopropanols, as stable yet powerful equivalents of the corresponding cyclopropanone derivatives, by α-hydroxylation of sulfonylcyclopropanes using a bis(silyl) peroxide as the electrophilic oxygen source. This work constitutes the first general approach to enantioenriched cyclopropanone derivatives. Both the electronic and steric nature of the sulfonyl moiety, which serves as a base-labile protecting group and confers crystallinity to these cyclopropanone precursors, were found to have a crucial impact on the rate of equilibration to the corresponding cyclopropanone. The utility of these cyclopropanone surrogates is demonstrated in a mild and stereospecific formal [3+1] cycloaddition with simple hydroxylamines, leading to the efficient formation of chiral β-lactam derivatives.
A general catalytic β-C-H carbonylation of aliphatic amines to β-lactams
Willcox, Darren,Chappell, Ben G. N.,Hogg, Kirsten F.,Calleja, Jonas,Smalley, Adam P.,Gaunt, Matthew J.
, p. 851 - 857 (2016/11/25)
Methods for the synthesis and functionalization of amines are intrinsically important to a variety of chemical applications. We present a general carbon-hydrogen bond activation process that combines readily available aliphatic amines and the feedstock gas carbon monoxide to form synthetically versatile value-added amide products. The operationally straightforward palladium-catalyzed process exploits a distinct reaction pathway, wherein a sterically hindered carboxylate ligand orchestrates an amine attack on a palladium anhydride to transform aliphatic amines into β-lactams. The reaction is successful with a wide range of secondary amines and can be used as a late-stage functionalization tactic to deliver advanced, highly functionalized amine products of utility for pharmaceutical research and other areas.
A Convenient Synthesis of Monocyclic β-Lactams by Means of Solid-Liquid Phase Transfer Reactions
Takahata, Hiroki,Ohnishi, Yoshinori,Takehara, Hiroyuki,Tsuritani, Kazuko,Yamazaki, Takao
, p. 1063 - 1068 (2007/10/02)
The intramolecular N-alkylation of β-bromopropionamides (1) under phase transfer conditions afforded monocyclic N-substituted β-lactams (2) in high yields.In a similar manner, cyclization by N1-C4 bond formation gave 4-benzoyl-2-azet
