698378-88-0

Upstream product

• 123-54-6 acetylacetone 
• 177896-09-2 tert-butyl benzylidenecarbamate 
• 150884-50-7 benzaldehyde N-boc imine 
• 100-52-7 benzaldehyde 
• 4248-19-5 tert-butyl carbazate 
• 1355078-52-2 di(tert-butyl) N,N'-benzylidenebis(carbamate) 

Downstream Products

• 1092775-20-6 (R)-(2-acetyl-1-phenyl-2-hydroxy-3-oxo-butyl)-carbamic acid tert-butyl ester 
• 143978-88-5 N-tert-butoxycarbonyl-L-phenylglycine methyl ester 
• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 

Relevant academic research and scientific papers

On the mechanism of stereoselection in direct Mannich reaction catalyzed by BINOL-derived phosphoric acids

Associates between the chiral phosphoric acids and Boc-protected imine were characterized computationally and by NMR; the primary importance of the bulky protecting group in imine for the high enantioselectivity in the direct Mannich reaction is rationali

A chiral organic base catalyst with halogen-bonding-donor functionality: Asymmetric Mannich reactions of malononitrile with: N -Boc aldimines and ketimines

A chiral organic base catalyst with halogen-bonding-donor functionality has been developed. This quinidine-derived acid/base catalyst smoothly promoted the asymmetric Mannich reaction of malononitrile and various N-Boc imines with up to 98% ee. The cooperative interaction with both substrates was responsible for the high activity that allowed a reduction of the catalyst amount to 0.5 mol%.

Decrypting Transition States by Light: Photoisomerization as a Mechanistic Tool in Br?nsted Acid Catalysis

Despite the wide applicability of enantioselective Br?nsted acid catalysis, experimental insight into transition states is very rare, and most of the mechanistic knowledge is gained by theoretical calculations. Here, we present an alternative approach (de

Acid-catalyzed in situ generation of less accessible or unprecedented N-Boc imines from N-Boc aminals

Crafty aminals: The in situ generation of hitherto unattainable alkynyl-substituted N-Boc-protected imines was realized by the acid-catalyzed elimination of tert-butyl carbamate from N-Boc aminals. A wide variety of N-Boc imines can be generated, which ca

BIS-PHOSPHATE COMPOUND AND ASYMMETRIC REACTION USING THE SAME

A novel bis-phosphate compound is provided which can be applied to a wide range of reactive substrates and reactions as an asymmetric reaction catalyst and can realize an asymmetric reaction affording a high yield and a high enantiomeric excess. The bis-p

Which is the actual catalyst: Chiral phosphoric acid or chiral calcium phosphate?

(Figure Presented) Both catalysts work: A highly enantioselective direct Mannich-type reaction of NBoc-protected aldimines with 1,3-dicarbonyl compounds has been developed with the use of a chiral phosphoric acid in the presence or absence of Ca . The absolute stereoselectivity of the phosphoric acid catalysis was found to be opposite to that of the calcium phosphate catalysis (see scheme; Boc = tert-butoxycarbonyl).

Highly practical BINOL-derived acid-base combined salt catalysts for the asymmetric direct mannich-type reaction

The catalytic asymmetric direct Mannich-type reaction between aldimines and 1,3-dicarbonyl compounds is one of the most important carbon-carbon bond-forming reactions in organic chemistry. The resulting Mannich adducts can be efficiently transformed into pharmaceutically useful, optically active -amino ketones, -amino esters, -lactams, etc. In the course of our study of chiral acid-base combined salt catalysts for asymmetric reactions, we developed a series of simple, practical, chiral BINOL-derived salt catalysts, such as chiral pyridinium 1,1-binaphthyl-2,2-disulfonates 1, chiral lithium(I) binaphtholate 2, chiral magnesium(II) binaphtholate (3), chiral calcium(II) phosphate 4, and chiral phosphoric acid 5, which were particularly effective for direct Mannich-type reactions. 1 Introduction 2 1,1-Binaphthyl-2,2-disulfonic Acid (BINSA)-Pyridinium Salts 3 Lithium(I) Binaphtholate Salts 4 Magnesium(II) Binaphtholate Salts 5 Calcium(II) Phosphate Salts and Chiral Phosphoric Acids 6 Conclusions. Georg Thieme Verlag Stuttgart · New York.

Chiral lithium(I) binaphtholate salts for the enantioselective direct Mannich-type reaction with a change of syn/anti and absolute stereochemistry

(Chemical Equation Presented) A highly diastereo- and enantioselective direct Mannich-type reaction of aldimines with 1,3-dicarbonyl compounds using Li(I) BINOLate salts as effective Lewis acid-Bronsted base catalysts has been developed. Li(I) BINOLate sa

PROCESS FOR PRODUCTION OF DISULFONIC ACID COMPOUND, ASYMMETRIC MANNICH CATALYST, PROCESS FOR PRODUCTION OF -AMINOCARBONYL DERIVATIVE, AND NOVEL DISULFONATE SALT

Hexamethylphosphoramide (HMPA) was added to a reaction vessel containing (R)-1,1'-binaphthyl-2,2'-dithiol and potassium hydroxide. The vessel was purged with oxygen and stirred at 80°C for 5 days under 7 atmospheres of oxygen. After being cooled to room temperature, the reaction product was purified to yield potassium (R)-1,1'-binaphthyl-2,2'-disulfonate. The (R)-1,1'-binaphthyl-2,2'-disulfonic acid obtained from the disulfonate and 2,6-diphenylpyridine were stirred in acetonitrile, and then the solvent was evaporated under reduced pressure. Subsequently, magnesium sulfate and distilled CH2Cl2 were added to the reaction product, and the mixture was stirred at room temperature for 30 minutes. The resulting solution was cooled to 0°C. Benzaldehyde imine whose nitrogen is protected with Cbz and subsequently acetyl acetone were dropped into the solution over a period of 1 hour. The resulting mixture was further stirred at 0°C for 30 minutes. A corresponding β-aminocarbonyl derivative was thus produced with an yield of 91% and an enantiomeric excess of 90% ee.

Thieme Chemistry Journal awardees - Where are they now? Bifunctional silver acetate catalyzed asymmetric Mannich-type reactions

Efficient bifunctional silver acetate catalyzed three asymmetric Mannich-type reactions with high reactivity, up to >95:5 diastereoselectivities and moderate to excellent enantioselectivities (up to 97% ee). External base is not required in this bifunctio