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A Flexible Asymmetric Synthesis of anti ‐1,2‐Sulfanyl Amines
Author(s) -
Enders Dieter,
Moll Alexander,
Schaadt Annette,
Raabe Gerhard,
Runsink Jan
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300249
Subject(s) - chemistry , stereocenter , electrophile , sulfanyl , alkylation , diastereomer , bond cleavage , stereochemistry , hydrazone , enantioselective synthesis , enantiomer , reagent , nucleophile , medicinal chemistry , organic chemistry , catalysis
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)