01754nas a2200181 4500008004100000245014100041210006900182260000800251300001400259490000700273520105300280100002201333700002001355700002401375700002401399700002401423856012501447 2019 eng d00aStereoselective construction of deoxy-cruciferane alkaloids by NHC-catalyzed intramolecular annulation of homoenolate with quinazolinone0 aStereoselective construction of deoxycruciferane alkaloids by NH cAUG a7135-71390 v173 a

Chiral N-heterocyclic carbene (NHC)-catalyzed intramolecular [3 + 2] annulation of enals with an unactivated imine moiety of quinazolinone via formal homoenolate cycloaddition has been demonstrated. It is an excellent approach for stereoselective syntheses of deoxy-cruciferane alkaloids comprising a biologically important pyrroloindoline scaffold. Notably, this is the first report on the NHC-catalyzed asymmetric intramolecular homoenolate annulation with cyclic N-acyl amidine.

1 aAhire, Milind, M.1 aPol, Mahesh, D.1 aKavale, Dattatry, S1 aGonnade, Rajesh, G.1 aMhaske, Santosh, B. uhttps://library.ncl.res.in/content/stereoselective-construction-deoxy-cruciferane-alkaloids-nhc-catalyzed-intramolecular00964nas a2200181 4500008004100000022001400041245011500055210006900170260000900239300001400248490000700262520029400269100002100563700002000584700002200604700002400626856013200650 2020 eng d a1477-052000aConstruction of unique SCF3-containing building blocks via allylic alkylation of Morita-Baylis-Hillman adducts0 aConstruction of unique SCF3containing building blocks via allyli cMAR  a2085-20930 v183 a

Lewis base-catalyzed allylic alkylation of Morita-Baylis-Hillman adducts with alpha-SCF3 ketones has been demonstrated. The developed strategy provides efficient access to a series of highly functionalized scaffolds featuring trifluoromethanesufinyl motif on a stereogenic carbon.

1 aHalder, Priyanka1 aPol, Mahesh, D.1 aAhire, Milind, M.1 aMhaske, Santosh, B. uhttps://library.ncl.res.in/content/construction-unique-scf3-containing-building-blocks-allylic-alkylation-morita-baylis-hillman01469nas a2200193 4500008004100000022001400041245017400055210006900229260000900298300001400307490000700321520070700328100002101035700002001056700002101076700002501097700002401122856012901146 2021 eng d a0022-326300aAnnulation of enals with carbamoylpropiolates via NHC-catalyzed enolate pathway: access to functionalized maleimides/iso-maleimides and synthesis of aspergillus FH-X-2130 aAnnulation of enals with carbamoylpropiolates via NHCcatalyzed e cJUL  a9466-94770 v863 aHerein we report the N-heterocyclic carbene (NHC)-catalyzed [3 + 2] annulation of alpha,beta-unsaturated aldehydes with carbamoylpropiolates via an unusual enolate pathway leading to the construction of highly functionalized maleimides or isomaleimides. The electronic effect imposed by the alkyl/aryl group present on the amide nitrogen of carbamoylpropiolates plays a crucial role in the selective formation of these important five-membered heterocyclic building blocks. The developed protocol is mild and tolerates a wide range of substituents on both substrates. The application of this protocol in the synthesis of the antibacterial natural product Aspergillus FH-X-213 has also been demonstrated.1 aViveki, Amol, B.1 aPol, Mahesh, D.1 aHalder, Priyanka1 aSonavane, Sameer, R.1 aMhaske, Santosh, B. uhttps://library.ncl.res.in/content/annulation-enals-carbamoylpropiolates-nhc-catalyzed-enolate-pathway-access-functionalized