34270-17-2

Upstream product

• 6203-08-3 methyl bicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 76637-59-7 (1S,4S)-2-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 72431-82-4 methyl 2-endo-acetamidobicyclo<2.2.1>hept-5-ene-2-exo-carboxylate 
• 72431-82-4 methyl 2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate 
• 131053-12-8 (-)-menthyl 2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate 
• 131053-13-9 2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylic acid 
• 542-92-7 cyclopenta-1,3-diene 
• 131234-09-8 2-endo-acetamidobicyclo<2.2.1>heptane-2-exo-carboxylic acid 

Relevant academic research and scientific papers

New and facile synthesis of aminobicyclo[22.1]heptane-2-carboxylic acids

Abstract A facile approach for the stereoselective synthesis of a- and b-2-aminobicyclo[2.2.1]heptane-2-carboxylic acid is described. Substrate-controlled α-carboxylation of norbonene monoester delivered the asymmetric diester intermediate with high diastereoselectivity (up to 35:1). Sequential chemoselective ester cleavage, Curtius rearrangement, and hydrolysis gave the a- and b-isomers of 2-aminobicyclo[2.2.1]heptane-2-carboxylic acid, respectively.

N-Fmoc-dehydroalanine: A versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids

The synthesis of polymer-supported N-Fmoc-dehydroalanine starting from S-protected cysteine via an oxidation/elimination strategy is described. Cycloaddition with a range of dienes afforded a range of conformationally constrained amino acids in moderate yields. The potential applications of this methodology to combinatorial libraries is discussed. (C) 2000 Elsevier Science Ltd.

Asymmetric Synthesis of Chiral Cyclic Amino Acids by Diels-Alder Reactions of (2S)- and (2R)-4-Methyleneoxazolidin-5-ones

The synthesis of chiral (2S)- and (2R)-4-methyleneoxazolidin-5-ones, in high enantiomeric purity from (S)-S-methylcysteine, and their highly exo-selective Diels-Alder reactions with cyclic dienes are described. (1R,2S,4S)-2-Aminobicycloheptane-2-ca

ASYMMETRIC SYNTHESIS OF CYCLOALIPHATIC α-AMINO ACIDS WITH A NORBORNANE SKELETON

The asymmetric synthesis of endo and exo 2-aminonorbornane-2-carboxylic acids is carried out via the Diels-Alder reaction between cyclopentadiene and (-)-menthyl N-acetyl-α,β-dehydroalaninate.It is shown that this dienophile is more reactive than the corresponding methyl ester, which opens the way for the use of chiral N-acetyl-α,β-dehydroalaninates as dienophiles in asymmetric Diels-Alder reactions.As high diastereofacial selectivity is obtained with what was previously considered a mediocre chiral auxiliary, the acetamido group must play an important role, which is discussed.

A SYNTHESIS OF 2-AMINONORBORNENE-2-CARBOXYLIC ACID DERIVATIVES BY DIELS-ALDER REACTION USING α,β-DEHYDROALANINATES AS A DIENOPHILE

The Diels-Alder reaction of N-acyl-α,β-dehydroalanine esters with cyclopentadiene afforded a mixture of the stereoisomers of acylaminonorbornene-2-carboxylic acid esters in good yields.