117681-86-4

Upstream product

• 4530-20-5 BOC-glycine 
• 65253-04-5 (-)-8-phenylmenthol 
• 151132-90-0 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)amino>-2,2-dideuterioacetate 
• 42492-65-9 N-(tert-butoxycarbonyl)glycine-2,2-d₂ 

Downstream Products

• 1268444-44-5 (-)-8-phenylmenthyl N-(1,3-dithiolan-2-ylidene)glycinate 
• 2900-27-8 2-(tert-butoxycarbonylamino)-2-phenylacetic acid 
• 760-84-9 L-leucine hydrochloride 
• 102089-74-7 tert-butyl 2-hydroxy-1-phenylethylcarbamate 
• 142121-48-0 tert-butyl (1-hydroxy-4-methylpentan-2-yl)carbamate 
• 169556-48-3 rac-tert-butyl (1-hydroxy-3-methylbutan-2-yl)carbamate 
• 147252-84-4 tert-butyl (1-hydroxypropan-2-yl)carbamate 
• 117049-13-5 tert-Butoxycarbonylamino-phenyl-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 117049-12-4 2-tert-Butoxycarbonylamino-4-methyl-pentanoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 117049-11-3 2-tert-Butoxycarbonylamino-3-methyl-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 117049-10-2 2-tert-Butoxycarbonylamino-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 25705-52-6 (R)-phenylglycine hydrochloride 
• 38329-34-9 (S)-α-amino-α-phenylacetic acid hydrochloride 
• 13139-15-6 Boc-DL-Leu-OH 

Relevant academic research and scientific papers

Dearomative [2,3] sigmatropic rearrangement of ammonium ylides followed by 1,4-elimination to form α-(ortho-vinylphenyl)amino acid esters

A base-induced dearomative [2,3] sigmatropic rearrangement of amino acid ester-derived ammonium salts followed by 1,4-elimination produced α-(ortho-vinylphenyl)amino acid esters. The reaction of azetidine-2-carboxylic acid-derived ammonium salt, (1S,2S,1′R)-3b, proceeded with a perfect N-to-C chirality transfer to afford α-(ortho-vinylphenyl)azetidine-2-carboxylic acid ester, (R)-5 (99% ee). On the other hand, the reaction of glycine-derived ammonium salt (R)-6a, which involves an efficient chirality transfer from a chiral benzylic carbon to an α-carbon of an ester carbonyl giving the optically active α-(ortho-vinylphenyl)glycine ester, (R)-8a (85% ee), was demonstrated. Although this dearomative [2,3] rearrangement followed by 1,4-elimination has limitations with regard to the structures of the substrates, our method provides unique access to substituted α-arylamino acid derivatives.

Synthesis of nitroaryl derivatives of glycine via oxidative nucleophilic substitution of hydrogen in nitroarenes

Carbanion of ethyl N-(1,3-dithiolan-2-ylidene)glycinate adds to activated nitroarenes mostly in para position to the nitro group. Subsequent oxidation of the resulting σH adducts with DDQ gave respective α-nitroarylated glycine derivatives in moderate yields. The reaction of esters of chiral alcohols such as (-)-menthol or (-)-8-phenylmenthol proceeds with a moderate or high diastereoselectivity leading to enantiomerically enriched nitroarylglycines. ARKAT-USA, Inc.

Asymmetric Sommelet-Hauser rearrangement of N-benzylic ammonium salts

(Chemical Equation Presented) [2,3] over [1,2]: The asymmetric Sommelet-Hauser rearrangement of an ammonium salt derived from N-benzylic proline-derived or N-benzylic glycine (-)-8-phenylmenthol ester is shown to proceed with remarkably high levels of stereoselectivity. The method provides unique and efficient access to optically active α-aryl amino acid derivatives.

Asymmetric aza-[2,3]-Wittig sigmatropic rearrangements: Chiral auxiliary control and formal asymmetric synthesis of (2S, 3R, 4R)-4-hydroxy-3- methylproline and (-)-kainic acid

A survey of 16 different chiral auxiliaries and a variety of strategies found that an (-)-8-phenylmenthol ester of a glycine derived migrating group can control the absolute stereochemistry of aza-[2,3]-Wittig sigmatropic rearrangements with diastereoselectivities of ca. 3 : 1 with respect to the auxiliary. In two specific examples, ca. 50% yields of enantiomerically pure products were obtained after chromatographic purification. These were synthetically manipulated with no erosion of stereochemistry into intermediates that completed formal asymmetric syntheses of (+)-HyMePro and (-)-kainic acid. The Royal Society of Chemisrry 2005.

Asymmetric induction in acyclic radical reactions: Enantioselective syntheses of (S)-2-deuterioglycine and (R)-2-deuterioglycine

The (-)-8-phenylmenthol esters of N-Boc-glycine and N-Boc-2,2-dideuterioglycine were brominated with N-bromosuccinimide and the bromo compounds were reduced with tri-n-butyldeuteriostannane and tri-n-butylstannane respectively, to give the chiral glycine derivatives in 90% optical yield. Hydrolysis yielded the amino acid without racemisation.

The asymmetric synthesis of α-amino acids via the addition of grignard reagents to imine derivatives

The ester-8-phenylmenthyl N-Boc-glycinate 5a, undergoes free radical bromination by N-bromosuccinimide to give 8-phenylmenthyl N-Boc-bromoglycinate 8. Treatment of the bromide 8 with a variety of Grignard reagents at low temperature gave 8-phenylmenthyl (S-N-Boc-2-alkylgrycinates with high diastereoselectivity. Conditions were found for the hydrolysis of these derivatives with no racemization of the resultant amino acid.

A STEREOSELECTIVE SYNTHESIS OF N-BOC-α-AMINO ALCOHOLS AND α-AMINO ACIDS

A sterteoselective synthesis of N-Boc-α-amino alcohols and α-amino acids via the addition of Grignard reagents to the chiral electrophilic glycine equivalent α-bromo-N-Boc-glycine(-)phenylmenthylester is described.