357417-35-7Relevant academic research and scientific papers
N-heterocyclic carbene-catalyzed enantioselective mannich reactions with α-aryloxyacetaldehydes
Kawanaka, Yasufumi,Phillips, Eric M.,Scheidt, Karl A.
supporting information; experimental part, p. 18028 - 18029 (2010/03/26)
(Chemical Equation Presented) N-Heterocyclic carbenes (NHCs) catalyze a new Mannich-type reaction to form β-amino acid derivatives in high yield and enantioselectivity. The reaction is initiated by the addition of an NHC to an C-aryloxyaldehyde followed by elimination of a phenoxide anion which generates an enol/enolate. A Mannich addition to a tosylimine proceeds with excellent control over enantioselectivity. In a new carbene catalysis concept, catalyst regeneration is promoted by return, or rebound, and acylation of the phenoxide group which served as the activating component in the first step of the catalytic cycle. The activated ester products formed in situ are manipulated to form a variety of useful compounds including β-amino acids, β-amino amides, and peptides.
A convenient synthetic route to enantiopure N-tosylazetidines from α-amino acids
Ghorai, Manas K.,Das, Kalpataru,Kumar, Amit
, p. 2471 - 2475 (2007/10/03)
A general and convenient synthetic route to various chiral 2-substituted- and 2,4-disubstituted-N-tosylazetidines (ee >99%) is described in good overall yields starting from chiral α-amino acids using very simple chemistry.
A novel synthesis of the macrocyclic spermidine alkaloid (+)-(S)-dihydroperiphylline
Sergeyev, Sergey A.,Hesse, Manfred
, p. 161 - 167 (2007/10/03)
A novel, short, and highly stereoselective synthesis of the macrocyclic spermidine alkaloid (+)-(S)-dihydroperiphylline (15) is described. The key synthetic steps were the stereoselective addition of the chiral amine 1 to the cinnamate 2 and cyclization o
Asymmetric synthesis of β-amino acids through application of chiral sulfoxide
Sivakumar,Babu,Bhat, Sujata V.
, p. 1095 - 1099 (2007/10/03)
This paper describes asymmetric synthesis of β-aminophenylpropionic acid through application of a homochiral sulfoxide auxiliary. High kinetically controlled (3R,2S,RS)-diastereoselectivity (-60°C) is achieved during addition of the lithium enolate of tert-butyl (+)-(R)-p-toluenesulfinylacetate to substituted N-(benzylidene)toluene-4-sulfonamides 2a-2d. The reductive cleavage of adduct 3a with sodium amalgam yielded tert-butyl 3-(toluene-4-sulfonamido)-3-phenylpropionate 5a, which was subjected to ester hydrolysis and subsequent detosylation with sodium in liquid ammonia to yield (S)-β-aminophenylpropionic acid in good yield and high 91% e.e.
