55056-86-5

Upstream product

• 72431-82-4 methyl 2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate 
• 72431-82-4 methyl 2-endo-acetamidobicyclo<2.2.1>hept-5-ene-2-exo-carboxylate 
• 76637-59-7 (1S,4S)-2-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 6203-08-3 methyl bicyclo[2.2.1]hept-5-ene-2-carboxylate 

Relevant academic research and scientific papers

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.

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.

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.