155996-65-9Relevant academic research and scientific papers
A Flexible Asymmetric Synthesis of anti-1,2-Sulfanyl Amines
Enders, Dieter,Moll, Alexander,Schaadt, Annette,Raabe, Gerhard,Runsink, Jan
, p. 3923 - 3938 (2007/10/03)
An efficient and flexible asymmetric synthesis of various protected anti-1,2-sulfanyl amines bearing two adjacent stereogenic centres is described. Key steps are the diastereoselective α-alkylation of α-sulfanylated acetaldehyde-SAMP-hydrazones with various electrophiles and subsequent nucleophilic 1,2-addition of organocerium reagents to the hydrazone CN double bond. The resulting hydrazines were converted into the title compounds with excellent diastereomeric and enantiomeric excesses (de and ee values ≥ 96%) by reductive N,N bond cleavage to remove the chiral auxiliaries and protection of the amino functions. The relative and absolute configurations were determined by NOE experiments and X-ray structure analysis. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Enantioselective Synthesis of 2-Sulfenylated Aldehydes: Alkylation of Sulfenylated Acetaldehyde SAMP-Hydrazones
Enders, Dieter,Schaefer, Thomas,Piva, Olivier,Zamponi, Andrea
, p. 3349 - 3362 (2007/10/02)
A practical and efficient enantioselective synthesis of 2-sulfenylated aldehydes (S)-6 is described, based on the α-alkylation of sulfenylated acetaldehyde SAMP hydrazones (S)-4, easily prepared from bromoacetaldehyde diethylacetal 1, thiols and (S)-1-amino-2-methoxymethyl-pyrrolidine (SAMP).A chemoselective oxidative cleavage of the intermediate SAMP hydrazones (S,S)-5 with ozone gives rise to the title compounds (S)-6 in good overall yields and high enantiomeric excess of up to 97percent.
