Search results for "EOS"
showing 10 items of 2714 documents
Total synthesis of the monoterpenes (−)-mintlactone and (+)-isomintlactone
1992
Abstract The first total stereodirected synthesis of the monoterpenes (−)-mintlactone and (+)-isomintlactone from the same chiral starting product is described. A stereoselective, radical-mediated ring closure was the key step in both syntheses.
Total synthesis of (−)-mintlactone
1991
Abstract The first total, stereodirected synthesis of (—)-mintlactone is described. A stereoselective, radical-mediated ring closure was the key step in the synthesis.
Microbial origin for pedogenic micrite associated with a carbonate paleosol (Champagne, France)
1999
Abstract Micro-rods have been observed in indurated carbonate horizons (30 cm thick) that overlie a periglacial chalk formation, in contact with the present-day soil (Champagne, France). They are numerous in the upper part of the hardened layers. Variations in micro-rod morphologies are related to progressive biomineralization of organic matter, transforming purely organic rods into calcite. Mineralized rods undergo diagenesis and their arrangement evolves from a random mesh fabric to recrystallized micritic platelets to microsparite. Two types of organic micro-rods have been observed: bacilliform and thread-like bacteria. Mineralogically, micro-rods are low-magnesian calcite. Crystallograp…
A molecular electron density theory study of the mechanism, chemo- and stereoselectivity of the epoxidation reaction of R -carvone with peracetic acid
2019
The epoxidation reaction of R-carvone 8 with peracetic acid 9 has been studied within the molecular electron density theory at the B3LYP/6-311(d,p) computational level. The chemo- and stereoisomeric reaction paths involving the two C–C double bonds of R-carvone 8 have been studied. DFT calculations account for the high chemoselectivity involving the C–C double bond of the isopropenyl group and the low diastereoselectivity, in complete agreement with the experimental outcomes. The Baeyer–Villiger reaction involving the carbonyl group of R-carvone 8 has also been analysed. A bonding evolution theory analysis of the epoxidation reaction shows the complexity of the bonding cha…
Stereoselective Synthesis and Structural Correction of the Naturally Occurring Lactone Stagonolide G
2010
A convergent synthesis of the structure proposed for the naturally occurring lactone stagonolide G is described. All three stereocenters were created with the aid of asymmetric Brown allylations. The lactone ring was built by means of a ring-closing metathesis (RCM). The synthetic and the natural compound differed in their spectral properties. A new structure is now proposed for stagonolide G and demonstrated by means of a chemical transformation.
Counterion's Effect on the Catalytic Activity of Zn-Prolinamide Complexes in Aldol Condensations
2012
The catalytic activity of complexes involving organic ligands and Lewis acids can be modulated by changing any of their components. In this work we have studied the influence on the stereoselectivity and catalytic activity exerted by the counterion of zinc salts employed as cocatalysts of L-prolinamide in aldol condensations. The structures of the complexes have been determined both in solution and in the solid state.
ChemInform Abstract: β-Branched α-Halo Carboxylic Acid Derivatives via Stereoselective 1,4-Addition of Dialkylaluminum Chlorides to α,. beta.-Unsatur…
2010
Stereoselective Synthesis of Fluorine-Containing β-Amino Acids
2005
ChemInform Abstract: New Strategy for the Stereoselective Synthesis of Fluorinated β-Amino Acids.
2010
Racemic and chiral nonracemic α-substituted and α-unsubstituted β-fluoroalkyl β-amino acid derivatives 6 and 9 have been synthesized in two steps starting from fluorinated imidoyl chlorides 1 and ester enolates. This approach is based on the chemical reduction of previously obtained γ-fluorinated β-enamino esters 4 by using ZnI2/NaBH4 in a nonchelated aprotic medium (dry CH2Cl2) as the reducing agent. A metal-chelated six-membered model has been suggested to explain the stereochemical outcome of the reduction reaction. The process takes place with high yields and with moderate to good diastereoselectivity. The best results related to diastereoselective reduction of chiral β-enamino esters 4…
Regio- and stereoselective synthesis of constrained enantiomeric β-amino acid derivatives
2008
Abstract Chlorosulfonyl isocyanate addition to (−)- and (+)-apopinene furnished monoterpene-fused β-lactams in highly regio- and stereospecific reactions. β-Lactams 5 and 13 exhibited reactivities similar to those of the cycloalkane-fused analogs and were easily converted to the β-amino acid and its protected derivatives. The base-catalyzed isomerization of the cis -amino ester afforded the corresponding trans -amino acid enantiomers in excellent yields. The complete isomerization is explained by the stability difference, which was estimated by ab initio calculations between the cis- and trans -diastereomers.