62381-17-3

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 95-46-5 2-methylphenyl bromide 
• 932-31-0 ortho-tolylmagnesium bromide 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 644-36-0 o-methylphenylacetic acid 
• 75-65-0 tert-butyl alcohol 
• 36805-97-7 N,N-dimethylformamide di-tert-butyl acetal 

Downstream Products

• 1350707-55-9 tert-butyl (1R,2S)-2-formyl-2-methyl-1-o-tolylcyclopropanecarboxylate 
• 1350707-77-5 (1R,2S)-tert-butyl 2-(hydroxymethyl)-2-methyl-1-o-tolylcyclopropanecarboxylate 
• 1350707-57-1 tert-butyl (1S,2R)-2-bromo-2-formyl-1-o-tolylcyclopropanecarboxylate 
• 1350707-59-3 tert-butyl (1S,2R)-2-chloro-2-formyl-1-o-tolylcyclopropanecarboxylate 
• 1350707-79-7 tert-butyl (1S,2R)-2-chloro-2-(hydroxymethyl)-1-o-tolylcyclopropanecarboxylate 
• 439118-41-9 2-bromomethylphenylacetic acid t-butyl ester 

Relevant academic research and scientific papers

Erratum: Oxazaborolidinium Ion-Catalyzed Cyclopropanation of α-Substituted Acroleins: Enantioselective Synthesis of Cyclopropanes Bearing Two Chiral Quaternary Centers (J. Am. Chem. Soc. (2011) 133:51 (20708?20711) DOI: 10.1021/ja209270e)

Pages 20709 and 20710. In the published version of the paper, the trans:cis ratios of 2w and 2x were reversed. The revised results were confirmed by NOE experiments and comparison of the optical rotation data with reported values after transformation. The

Synthesis of Rhodium Complexes with Chiral Diene Ligands via Diastereoselective Coordination and Their Application in the Asymmetric Insertion of Diazo Compounds into E?H Bonds

A new method for the synthesis of chiral diene rhodium catalysts is introduced. The readily available racemic tetrafluorobenzobarrelene complexes [(R2-TFB)RhCl]2 were separated into two enantiomers via selective coordination of one of them with the auxiliary S-salicyl-oxazoline ligand. One of the resulting chiral complexes with an exceptionally bulky diene ligand [(R,R-iPr2-TFB)RhCl]2 was an efficient catalyst for the asymmetric insertion of diazoesters into B?H and Si?H bonds giving the functionalized organoboranes and silanes with high yields (79–97 %) and enantiomeric purity (87–98 % ee). The stereoselectivity of separation via auxiliary ligand and that of the catalytic reaction was predicted by DFT calculations.

Catalytic Asymmetric Darzens-Type Epoxidation of Diazoesters: Highly Enantioselective Synthesis of Trisubstituted Epoxides

Highly enantioselective Darzens-type epoxidation of diazoesters with glyoxal derivatives was accomplished using a chiral boron–Lewis acid catalyst, which facilitated asymmetric synthesis of trisubstituted α,β-epoxy esters. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99 %) with excellent enantio- and diastereoselectivity (up to >99 % ee and >20:1 dr, respectively). The synthetic potential of this method was illustrated by conversion of the products to various compounds such as epoxy γ-butyrolactone, tertiary β-hydroxy ketone and epoxy diester.

Cu(I)/chiral bisoxazoline-catalyzed enantioselective sommelet-hauser rearrangement of sulfonium ylides

Catalytic asymmetric thia-Sommelet-Hauser rearrangement of sulfonium ylides remains a great challenge due to its multistep reaction mechanism involving metal carbene formation, proton transfer, and [2,3]-sigmatropic rearrangement. In particular, the key problem of such reactions is the differentiation of the enantiotopic lone pair electrons of sulfur, which generates the sulfonium ylide intermediate bearing chirality on the sulfur atom. With a modified chiral bisoxazoline ligand, we developed a Cu(I)- catalyzed asymmetric thia-Sommelet-Hauser rearrangement with good to excellent enantioselectivities. Mechanistic studies provide insights into the details of the reaction mechanism.

Synthesis and complexing properties of cyclic benzylopeptoids-a new family of extended macrocyclic peptoids

An efficient protocol for the solid-phase synthesis of six members of a new class of extended macrocyclic peptoids (based on ortho-, meta- and para-N-(methoxyethyl)aminomethyl phenylacetyl units) is described. Theoretical (DFT) and experimental (NMR) studies on the free and Na+-complexed cyclic trimers (3-5) and tetramers (6-8) demonstrate that annulation of the rigidified peptoids can generate new hosts with the ability to sequestrate one or two sodium cations with the affinities and stoichiometries defined by the macrocycle morphology. Ion transport studies have been also performed in order to better appreciate the factors promoting transmembrane cation translocation.

Palladium-catalyzed α-arylation of zinc enolates of esters: Reaction conditions and substrate scope

The intermolecular α-arylation of esters by palladium-catalyzed coupling of aryl bromides with zinc enolates of esters is reported. Reactions of three different types of zinc enolates have been developed. α-Arylation of esters occurs in high yields with i

Oxazaborolidinium ion-catalyzed cyclopropanation of α-substituted acroleins: Enantioselective synthesis of cyclopropanes bearing two chiral quaternary centers

A catalytic synthetic route to highly functionalized chiral cyclopropane derivatives was developed by Michael-initiated cyclopropanation of α-substituted acroleins with aryl- and alkyl diazoacetates. In the presence of chiral (S)-oxazaborolidinium cation

Iron-catalyzed chemoselective cross-coupling of α-bromocarboxylic acid derivatives with aryl grignard reagents

We have developed a simple and effective synthetic method of α-arylcarboxylic acid derivatives based on the iron-catalyzed cross-coupling reaction of α-bromocarboxylic acid derivatives with aryl Grignard reagents. The reaction proceeds smoothly at -78 °C in a chemoselective manner to produce the coupling product in good to excellent yields.

Identification of potent and novel small-Molecule inhibitors of caspase-3

The design and synthesis of a series of novel, reversible, small molecule inhibitors of caspase-3 are described.

Palladium-catalyzed α-arylation of esters

A new and simple one-pot procedure for the palladium-catalyzed intermolecular α-arylation of esters is described. A number of esters can be functionalized with a wide range of aryl bromides using Pd(OAc)2 or Pd2(dba)3 and