35719-58-5Relevant academic research and scientific papers
New and facile synthesis of aminobicyclo[22.1]heptane-2-carboxylic acids
Kim, Taek-Soo,Seo, Seung-Yong,Shin, Dongyun
supporting information, p. 1243 - 1247 (2015/03/31)
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
Burkett,Chai
, p. 6661 - 6664 (2007/10/03)
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 2-Aminonorbornane-2-carboxylic acids by Diels-Alder reaction
Cativiela,Lopez,Mayoral
, p. 61 - 64 (2007/10/02)
Reaction of (-)-menthyl N-acetyl-α,β-dehydroalaninate with cyclopentadiene takes place with good chemical yields and diastereofacial selectivity. The cycloadducts are easily transformed into the corresponding amino acids.
ASYMMETRIC SYNTHESIS OF CYCLOALIPHATIC α-AMINO ACIDS WITH A NORBORNANE SKELETON
Cativiela, Carlos,Lopez, Pilar,Mayoral, Jose A.
, p. 379 - 388 (2007/10/02)
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
Horikawa, Hiroshi,Nishitani, Takashi,Iwasaki, Tameo,Mushika, Yoshitaka,Inoue, Ichizo,Miyoshi, Muneji
, p. 4101 - 4104 (2007/10/02)
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.
