183990-48-9

Upstream product

• 124-38-9 carbon dioxide 
• 183990-21-8 ((R)-1-Chloromethyl-propyl)-carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 183990-19-4 ((S)-1-Chloromethyl-propyl)-carbamic acid tert-butyl ester 
• 371976-48-6 (R)-dimethyl 2-((2,2,2-trifluoroacetylamino)propyl)propane-1,3-dioate 
• 138587-72-1 syn-3-ethyl-5-(1-hydroxyethyl)-4,5-dihydroisoxazole 
• 186581-53-3 diazomethane 
• 34306-42-8 Boc-Abu 
• 271600-09-0 [(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propyl]-carbamic acid benzyl ester 
• 147169-21-9 tert-butyl N-<1-((p-methylphenyl)sulfonyl)propyl>carbamate 
• 623582-49-0 (R)-2-((3S,5R)-3-Ethyl-5-hydroxymethyl-isoxazolidin-2-yl)-2-phenyl-ethanol 
• 623582-56-9 ((1S,3R)-1-Ethyl-3,4-dihydroxy-butyl)-carbamic acid tert-butyl ester 
• 271600-10-3 [(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Succinct synthesis of β-amino acids via chiral isoxazolines

β-Amino acids are important synthetic targets due to their presence in a wide variety of natural products, pharmaceutical agents, and mimics of protein structural motifs. While β-amino acids containing geminal substitution patterns have enormous potential for application in these contexts, synthetic challenges to the stereoselective preparation of this class of compound have thus far limited more complete studies. We present here a straightforward method employing chiral isoxazolines as key intermediates to access five different β-amino acid structural types with excellent selectivity. Of particular note is the use of this approach to prepare highly substituted cis-β-proline analogues. The ready access to these diversely substituted compounds is expected to facilitate future studies of the structure and function of this important class of molecules.

A concise approach to structurally diverse β-amino acids

We have demonstrated that the high yields and selectivities of 1,3-dipolar cycloadditions can be translated into facile stereoselective syntheses of a diverse array of β-amino acids, key components of bioactive natural products, β-lactams, and peptidomimetics. Simply by selecting different combinations of three readily available starting materials (an oxime, a chiral allylic alcohol, and a nucleophile), we used the reaction sequence to prepare four different β-amino acid structural types with a variety of substitution patterns in good overall yield. Of particular note is the use of this approach to prepare highly substituted β-amino acids not readily accessible by previously reported methodologies. This will pave the way for future studies of the structure and function of this important class of molecules. Copyright

Synthesis of Cyclic and Acyclic β-Amino Acids via Chelation-Controlled 1,3-Dipolar Cycloaddition

Isoxazolidines have been synthesized in diastereomeric excess up to 94% via a MgBr2-induced chelation-controlled 1,3-dipolar cycloaddition reaction with N-hydroxyphenylglycinol as a chiral auxiliary. The diastereomerically pure isoxazolidines were further transformed into cyclic and acyclic β-amino acid derivatives.

α-Oxymethyl ketone enolates for the asymmetric Mannich reaction. From acetylene and N-alkoxycarbonylimines to β-amino acids

The insufficient diastereoselectivity and generality, which are the main problems of the 'acetate' aza - aldol reaction, can now be addressed through the reaction of the lithium enolate of endo-O-trimethylsilyl acetyl isoborneol with various N[(p-tolylsul

EPC-synthesis of functionalised amides via chiral β-nitrogenated organolithium compounds

The deprotonation of chiral chloroamides or carbamates 1, 4, 7, 10, 13 and 16 with n-butyllithium followed by in situ lithiation with lithium naphthalenide, both at -78°C in THF, leads to the formation of the corresponding chiral dianionic intermediates,