402755-63-9

Upstream product

• 88-65-3 2-bromobenzoic-acid 
• 20859-02-3 L-tert-Leucine 
• 112245-13-3 (S)-tert-leucinol 
• 7154-66-7 2-bromobenzoic acid chloride 

Downstream Products

• 154701-60-7 2-(2-bromophenyl)-4-(1,1-dimethylethyl)-4,5-dihydro-(4S)-oxazole 
• 148461-16-9 (S)-4-(tert-butyl)-2-(2-(diphenylphosphaneyl)phenyl)-4,5-dihydrooxazole 
• 1374010-11-3 C₃₂H₃₇N₂O₃P 
• 297746-06-6 [2-[(4S)-4-(tert-butyl-1,3-oxazolin-2-yl)]phenyl]diphenylphosphino-1-one 
• 1195945-63-1 (S)-2-(2-bromophenyl)-4-tert-butyl-4,5-dihydrothiazole 
• 716368-89-7 (4S)-tert-butyl-2-[2-(3-phenyl-allylselanyl)-phenyl]-4,5-dihydro-oxazole 
• 104713-12-4 (1S)-1-phenylprop-2-en-1-ol 
• 104713-12-4 (R)-1-phenylprop-2-en-1-ol 

Relevant academic research and scientific papers

Enantioselective Allylic C?H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis

The enantioselective synthesis of isochroman motifs has been accomplished by palladium(II)-catalyzed allylic C?H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sul

Synthesis of chiral S,N-thioimidazoline ligands for palladium-catalyzed asymmetric allylic alkylations

A series of chiral S,N-thioimidazoline ligands have been synthesized using 2-bromobenzoic acid or 1-bromo-2-naphthoic acid as starting materials. The obtained ligands were evaluated in the Pd-catalyzed asymmetric allylic alkylations and exhibited high catalytic efficiency: yields of up to 94% and enantioselectivities of up to 86% were achieved under the optimized conditions.

The synthesis of phosphine oxide-linked bis(oxazoline) ligands and their application in asymmetric allylic alkylation

The phosphine oxide-linked bis(oxazoline) ligands were designed and synthesized in two ways. One is the coupling of Grignard reagent derived from 2-(2-bromophenyl)oxazoline with phenylphosphonic dichloride, another route is the condensation of bis(2-formylphenyl)(phenyl)phosphine oxide with chiral amino alcohols followed by NBS oxidation. These new bis(oxazoline) ligands were applied in Pd-catalyzed asymmetric allylic alkylation reactions and good yields and enantioselectivities were obtained with diphenyl substituted ligand (up to 95% ee).

Enantioselective decarboxylative alkylation reactions: Catalyst development, substrate scope, and mechanistic studies

α-Quaternary ketones are accessed through novel enantioselective alkylations of allyl and propargyl electrophiles by unstabilized prochiral enolate nucleophiles in the presence of palladium complexes with various phosphinooxazoline (PHOX) ligands. Excellent yields and high enantiomeric excesses are obtained from three classes of enolate precursor: enol carbonates, enol silanes, and racemic β-ketoesters. Each of these substrate classes functions with nearly identical efficiency in terms of yield and enantioselectivity. Catalyst discovery and development, the optimization of reaction conditions, the exploration of reaction scope, and applications in target-directed synthesis are reported. Experimental observations suggest that these alkylation reactions occur through an unusual inner-sphere mechanism involving binding of the prochiral enolate nucleophile directly to the palladium center. Sly as a PHOX: The development of an enantioselective decarboxylative palladium-catalyzed allylic alkylation reaction, utilizing phosphinooxazoline ligands, is described. The catalyst is applied to a range of allyl enol carbonate, silyl enol ether, and allyl β-ketoester substrates to provide alkylated ketone products in excellent yield and good ee (see scheme). The utility of these products is demonstrated by their use in several asymmetric syntheses. Mechanistic studies are reported suggesting an unusual inner-sphere mechanism. Copyright

New thiazoline-oxazoline ligands and their application in the asymmetric friedel-crafts reaction

Six members of a novel non-C2-symmetric ligand class incorporating an oxazoline and. thiazoline unit have been prepared in a four-step, high-yielding and. convergent: synthesis, in which the key step is a microwave-assisted palladium-catalyzed

A facile and modular synthesis of phosphinooxazoline ligands

The copper(I) iodide catalyzed phosphine/aryl halide coupling procedure of Buchwald et al. provides modular, robust, and scaleable access to phosphinooxazoline (PHOX) ligands. The advantages of this method are highlighted by the convenient synthesis of PH

Catalytic asymmetric hydrogenation of N-iminopyridinium ylides: Expedient approach to enantioenriched substituted piperidine derivatives

We have developed an efficient catalytic enantioselective hydrogenation of pyridine derivatives. Enhanced reactivity was possible by an optimization of the electronic properties of the catalyst through ligand modification. This methodology shows the parti

The enantioselective Tsuji allylation

The first catalytic enantioselective examples of the Tsuji allylation using enol carbonates and enol silanes are described. The products possess a quaternary stereogenic center and are useful building blocks for synthetic chemistry. Copyright

Vanadium-catalyzed selenide oxidation with in situ [2,3] sigmatropic rearrangement (SOS reaction): Scope and asymmetric applications

A vanadium-catalyzed method for the oxidation of prochiral aryl, allylic selenides with tandem sigmatropic rearrangement has been developed. This protocol has been screened on a series of substrates to test for its generality and effectiveness. The applicability of this methodology to the synthesis of enantiomerically enriched allylic alcohols has been studied on a series of chiral oxazole-containing systems with a diastereomeric ratio (d.r.) of up to 85 : 15. The chiral transfer observed in the allyl alcohol products is the result of a net 1,9- and/or 1,10-induction. Finally, the first example of a selenium-oxygen nonbonding interaction in oxazole-containing selenide appears to have been observed via X-ray crystal analysis.