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Synthesis and Reactivities of Enantiomerically Pure β‐Hydroxyalkyl and β‐Aminoalkyl Ferrocenyl Sulfides
Author(s) -
Bernardi Luca,
Bonini Bianca F.,
ComesFranchini Mauro,
Fochi Mariafrancesca,
Mazzanti Germana,
Ricci Alfredo,
Varchi Greta
Publication year - 2002
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 - 10.1002/1099-0690(200208)2002:16<2776::aid-ejoc2776>3.0.co;2-y
Subject(s) - chemistry , moiety , ferrocene , allylic rearrangement , palladium , asymmetric induction , alcohol , sulfide , organic chemistry , enantioselective synthesis , medicinal chemistry , stereochemistry , catalysis , electrochemistry , electrode
Enantiomerically pure β‐hydroxyalkyl and β‐aminoalkyl ferrocenyl sulfides have been synthesized in good yields from mercaptoferrocene and amino alcohol derivatives. Primary β‐aminoalkyl sulfides allowed the synthesis of tetrahydro‐1,4‐thiazepines containing the ferrocene moiety with good diastereoselectivity and β‐iminoalkyl sulfides. Some of these derivatives have successfully been employed as ligands for palladium‐catalyzed allylic substitution, with asymmetric induction of up to 99% ee . (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)