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Enantioselective Synthesis of β‐Necrodol and of 1‐Epi‐β‐necrodol via Asymmetric 1,4‐Addition and Magnesium‐Ene Cyclization. Preliminary Communication
Author(s) -
Oppolzer Wolfgang,
Schneider Philippe
Publication year - 1986
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.19860690805
Subject(s) - chemistry , enantioselective synthesis , conjugate , ene reaction , epimer , aldehyde , tandem , magnesium , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , mathematical analysis , materials science , mathematics , composite material
Enantiomerically pure β‐necrodol ( 1 ) and its 1‐epimer 16 have been synthesized starting from aldehyde 5 . The two key steps are an asymmetric conjugate addtion/ Mannich reaction tandem ( 10 → 12 ) and a type‐II‐magnesiumene cyclization/oxidation sequence ( 14 → 1 + 16 ).