20448-80-0

Upstream product

• 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 
• 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 

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.

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.