Synthesis of chiral 3-substituted 3-amino-2-oxindoles through enantioselective catalytic nucleophilic additions to isatin imines
- Hélène Pellissier
Beilstein J. Org. Chem. 2018, 14, 1349–1369, doi:10.3762/bjoc.14.114
Graphical Abstract
Scheme 1: Mannich reaction of N-Boc-isatin imines with ethyl nitroacetate (2) catalyzed by a cinchona alkaloi...
Scheme 2: Mannich reaction of N-Boc-isatin imines with 1,3-dicarbonyl compounds catalyzed by a cinchona alkal...
Scheme 3: Mannich reaction of N-alkoxycarbonylisatin imines with acetylacetone catalyzed by a cinchona alkalo...
Scheme 4: Mannich reaction of isatin-derived benzhydrylketimines with trimethylsiloxyfuran catalyzed by a pho...
Scheme 5: Mannich reaction of N-Boc-isatin imines with acetaldehyde catalyzed by a primary amine.
Scheme 6: Mannich reaction of N-Cbz-isatin imines with aldehydes catalyzed by L-diphenylprolinol trimethylsil...
Scheme 7: Addition of dimedone-derived enaminones to N-Boc-isatin imines catalyzed by a phosphoric acid.
Scheme 8: Addition of hydroxyfuran-2-one-derived enaminones to N-Boc-isatin imines catalyzed by a phosphoric ...
Scheme 9: Zinc-catalyzed Mannich reaction of N-Boc-isatin imines with silyl ketene imines.
Scheme 10: Tin-catalyzed Mannich reaction of N-arylisatin imines with an alkenyl trichloroacetate.
Scheme 11: Aza-Morita–Baylis–Hillman reaction of N-Boc-isatin imines with acrolein catalyzed by β-isocupreidin...
Scheme 12: Aza-Morita–Baylis–Hillman reaction of N-Boc-isatin imines with acrolein (35) catalyzed by α-isocupr...
Scheme 13: Aza-Morita–Baylis–Hillman reaction of N-Boc-isatin imines with maleimides catalyzed by β-isocupreid...
Scheme 14: Aza-Morita–Baylis–Hillman reaction of N-Boc-isatin imines with nitroolefins catalyzed by a cinchona...
Scheme 15: Friedel–Crafts reactions of N-Boc-isatin imines with 1 and 2-naphthols catalyzed by a cinchona alka...
Scheme 16: Friedel–Crafts reactions of N-alkoxycarbonyl-isatin imines with 1 and 2-naphthols catalyzed by a ci...
Scheme 17: Friedel–Crafts reaction of N-Boc-isatin imines with 6-hydroxyquinolines catalyzed by a cinchona alk...
Scheme 18: Aza-Henry reaction of N-Boc-isatin imines with nitromethane catalyzed by a bifunctional guanidine.
Scheme 19: Domino addition/cyclization reaction of N-Boc-isatin imines with 1,4-dithiane-2,5-diol (53) catalyz...
Scheme 20: Nickel-catalyzed additions of methanol and cumene hydroperoxide to N-Boc-isatin imines.
Scheme 21: Palladium-catalyzed addition of arylboronic acids to N-tert-butylsulfonylisatin imines.
Recent developments in the asymmetric Reformatsky-type reaction
- Hélène Pellissier
Beilstein J. Org. Chem. 2018, 14, 325–344, doi:10.3762/bjoc.14.21
Graphical Abstract
Scheme 1: Reformatsky-type reaction.
Scheme 2: First total synthesis of prunustatin A based on a Zn-mediated Reformatsky reaction [17].
Scheme 3: Synthesis of a γ-hydroxylysine derivative through a Zn-mediated nitrile Reformatsky-type reaction [18].
Scheme 4: Synthesis of apratoxin E and its C30 epimer through a Zn-mediated Reformatsky reaction. Fmoc = 9-fl...
Scheme 5: Synthesis of the eastern fragment of jatrophane diterpene Pl-3 through a SmI2-mediated Reformatsky ...
Scheme 6: First total synthesis of prebiscibactin through a SmI2-mediated Reformatsky reaction. Boc = tert-bu...
Scheme 7: Synthesis of prostaglandin E2 methyl ester through a SmI2-mediated Reformatsky reaction [23].
Scheme 8: Synthesis of the C1–C11 fragment of tedanolide C through a SnCl2-mediated Reformatsky reaction. PMB...
Scheme 9: Synthesis of β-trifluoromethyl β-(N-tert-butylsulfinyl)amino esters exhibiting a quaternary stereoc...
Scheme 10: Synthesis of α,α-difluoro-β-(N-tert-butylsulfinyl)amino esters through Zn(II)-mediated aza-Reformat...
Scheme 11: Synthesis of a common fragment to anti-apoptotic protein inhibitors through a Zn-mediated aza-Refor...
Scheme 12: Synthesis of α,α-difluoro-β-(N-tert-butylsulfinyl)amino ketones through a Zn-mediated aza-Reformats...
Scheme 13: Synthesis of (2-oxoindolin-3-yl)amino esters through a Zn-mediated aza-Reformatsky reaction [30].
Scheme 14: Synthesis of a precursor of sacubitril through a Zn-mediated aza-Reformatsky reaction [31].
Scheme 15: Synthesis of epothilone D through a Cr(II)-mediated Reformatsky reaction. TFA = trifluoroacetic aci...
Scheme 16: Synthesis of β-hydroxy-α-methyl-δ-trichloromethyl-δ-valerolactone through a Sm(II)- or Yb(II)-media...
Scheme 17: Synthesis of cebulactam A1 through a Sm(II)-mediated Reformatsky reaction. MOM = methoxymethyl [34].
Scheme 18: Synthesis of ansamacrolactams (+)-Q-1047H-A-A and (+)-Q-1047H-R-A through a Sm(II)-mediated Reforma...
Scheme 19: Reformatsky reaction of aldehydes with ethyl iodoacetate in the presence of a chiral 1,2-amino alco...
Scheme 20: Reformatsky reaction of aldehydes with ethyl bromoacetate in the presence of a chiral amide ligand [44]....
Scheme 21: Reformatsky reaction of cinnamaldehyde with ethyl bromozinc-α,α-difluoroacetate in the presence of ...
Scheme 22: Reformatsky reaction of aldehydes with an enolate equivalent prepared from phenyl isocyanate and CH2...
Scheme 23: Domino aza-Reformatsky/cyclization reactions of imines with ethyl dibromofluoroacetate in the prese...
Scheme 24: Domino aza-Reformatsky/cyclization reactions of imines with ethyl bromodifluoroacetate in the prese...
Scheme 25: Aza-Reformatsky reactions of cyclic imines with ethyl iodoacetate in the presence of a chiral diary...
Scheme 26: Mechanism for aza-Reformatsky reaction of cyclic imines with ethyl iodoacetate in the presence of a...
Scheme 27: Aza-Reformatsky reaction of dibenzo[b,f][1,4]oxazepines and dibenzo[b,f][1,4]thiazepine with ethyl ...
