936724-71-9Relevant academic research and scientific papers
Synthesis of enantiomerically enriched α,α-disubstituted β,γ-epoxy esters using hydrolytic kinetic resolution catalyzed by salenCo(III)
Viera, Ignacio,Manta, Eduardo,Gonzalez, Lucia,Mahler, Graciela
experimental part, p. 631 - 635 (2010/08/03)
Novel α,α-disubstituted epoxy esters were prepared in enantiopure form by hydrolytic kinetic resolution (HKR) of the corresponding racemic mixtures using chiral salenCo(III) as catalyst. The methodology provides a convenient route to enantioenriched β,γ-epoxy esters 2a, 2c and 2d.
Intramolecular cyclopropanation of unsaturated terminal epoxides and chlorohydrins
Hodgson, David M.,Ying, Kit Chung,Nuzzo, Irene,Freixas, Gloria,Kulikiewicz, Krystyna K.,Cleator, Ed,Paris, Jean-Marc
, p. 4456 - 4462 (2008/02/02)
Lithium 2,2,6,6-tetramethylpiperidide (LTMP)-induced intramolecular cyclopropanation of unsaturated terminal epoxides provides an efficient and completely stereoselective entry to bicyclo[3.1.0]hexan-2-ols and bicyclo[4.1.0]heptan-2-ols. Further elaboration of C-5 and C-6 stannyl-substituted bicyclo[3.1.0]-hexan-2-ols via Sn-Li exchange/electrophile trapping or Stille coupling generates a range of substituted bicyclic cyclopropanes. An alternative straightforward cyclopropanation protocol using a catalytic amount of 2,2,6,6-tetramethylpiperidine (TMP) allows for a convenient (1 g-7.5 kg) synthesis of bicyclo[3.1.0]-hexan-2-ol and other bicyclic adducts. The synthetic utility of this chemistry has been demonstrated in a concise asymmetric synthesis of (+)-β-cuparenone. The related unsaturated chlorohydrins also undergo intramolecular cyclopropanation via in situ epoxide formation.
Regioselective synthesis of 3,3-diethyl-4-(methylene)-1-quinol-2-ones by an intramolecular microwave assisted heck reaction
Smalley Jr., Terrence L.,Mills, Wendy Y.
, p. 327 - 331 (2007/10/03)
A protocol for the intramolecular Heck cyclization to afford 3,3-diethyl-4-(methylene)-1-quinol-2-ones is described. We observed that the use of microwave irradiation increased the efficiency of the reaction. Several examples are presented which show the
