40216-78-2Relevant academic research and scientific papers
Facile synthesis of highly functionalized N-methyl amino acid esters without side-chain protection
White, Kimberly N.,Konopelski, Joseph P.
, p. 4111 - 4112 (2007/10/03)
(Chemical Equation Presented) The facile, two-pot synthesis of N-methyl amino acid esters by way of reductive amination is presented. Side chain protection schemes are not required, the starting materials are all commercially available, and the synthetic
Stereoselective Addition of Dimethyl Thiophosphite to Imines
Tongcharoensirikul, Pakamas,Suarez, Alirica I.,Voelker, Troy,Thompson, Charles M.
, p. 2322 - 2326 (2007/10/03)
Dimethyl thiophosphite (DMTP) was synthesized from dimethyl phosphite, and the diastereoselective addition of DMTP to benzaldimines bearing chiral auxiliary groups was examined. Yields of the product α -aminophosphonothionates ranged from 17% to 75% after chromatography. The addition of DMTP to the benzaldimine derived from (S)-phenylglycinol afforded the highest diastereoselectivity (83:17), whereas addition of DMTP to the benzaldimine derived from threonine methyl ester and alanine methyl ester were far less diastereoselective, affording 38:62 and 61:39 ratios, respectively. Addition of DMTP to the benzaldimine derived from (R)-α-methylbenzylamine (78:22) and (S)-serine methyl ester (73:27) were intermediate in selectivity. DMTP addition to the imines formed between serine methyl ester and acetaldehyde and isobutyraldehyde gave 55:45 and 70:30 ratios, respectively, with the diastereoselectivity corresponding roughly to the size of the α-alkyl group. The stereochemistry of the newly formed α-stereocenters resulting from the addition of DMTP to (S)- and (R)-phenylglycinol benzaldimines was confirmed by conversion of the product α-aminophosphonothionates to the known enantiomers of phosphonophenylglycine.
N-methyl threonine analogues of deglycobleomycin A2: Synthesis and evaluation
Boger, Dale L.,Teramoto, Shuji,Cai, Hui
, p. 1577 - 1589 (2007/10/03)
The synthesis of 5 and its D-allo-threonine epimer 6 and the comparison of their DNA cleavage efficiency and selectivity with that of deglycobleomycin A2 (3) are detailed. The studies illustrate that N-methylation of the L-threonine subunit wit
Stereoselective synthesis of β-lactams by condensation of titanium enolates of 2-pyridyl thioesters with imines bearing a chiral auxiliary
Annunziata, Rita,Benaglia, Maurizio,Cinquini, Mauro,Cozzi, Franco,Raimondi, Laura
, p. 9471 - 9486 (2007/10/02)
Several amines have been tested as chiral auxiliaries in the stereoselective synthesis of β-lactams by condensation of the titanium enolates of 2-pyridyl thioesters with chiral imines. The amines were selected among the following classes of compounds: ben
