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Enantioselective Synthesis of Both Enantiomers of a Isoproterenol Analogue and of Di‐ O ‐pivaloylepinephrine
Author(s) -
SolladiéCavallo Arlette,
SimonWermeister MarieClaude,
Farkhani Dariouch
Publication year - 1991
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19910740216
Subject(s) - chemistry , enantioselective synthesis , enantiomer , stereochemistry , reduction (mathematics) , combinatorial chemistry , organic chemistry , catalysis , geometry , mathematics
Abstract An asymmetric synthesis of the analogue 4a of isoproterenol and of di‐ o ‐pyvaloylepinephrine 3 which provides both enantiomers in optically pure state is reported. The key step of the method is the highly diastereo‐selective reduction (using DIBAL or DIBAL/ZnCl 2 ) of a β‐ketosulfoxide 7 which leads, as desired, to the ( S )‐ or the ( R )‐configuration at C(1) ( Schemes 4 and 5 ).