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Bridging the Final Gap in Stereocontrolled Wittig Reactions: Methoxymethoxy‐Armed Allylic Phosphorus Ylides Affording Conjugated Dienes with High cis Selectivity
Author(s) -
Wang Qian,
El Khoury Mirella,
Schlosser Manfred
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(20000204)6:3<420::aid-chem420>3.0.co;2-h
Subject(s) - phosphonium , phosphine oxide , wittig reaction , chemistry , allylic rearrangement , conjugated system , phosphine , steric effects , amide , toluene , butyllithium , hydrolysis , tris , organic chemistry , medicinal chemistry , selectivity , catalysis , biochemistry , polymer
Chemists must learn patience . It took more than 30 years from the discovery of the first highly cis ‐selective Wittig reactions to close the last remaining gap. Allylic phosphorus ylides carrying methoxymethoxy arms at the ortho positions react with aldehydes affording conjugated dienes (shown here) in moderate yields and excellent Z / E ratios (averaging 96:4).