- Regio- and Stero-selective Desulphurizative γ-Substitution of α-Substituted β-Methylallyl Sulphoxides and Sulphones with Lithium Dialkylcuprates providing Trisubstituted Olefins
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α-Substituted β-methylallyl sulphoxides (2) and sulphones (3) undergo regio- and stereo-selective desulphurizative γ-substitution by the action of lithium dialkylcuprates in ether.The reaction provides a new method for the synthesis of trisubstituted E-ol
- Masaki, Yukio,Sakuma, Kazuhiko,Kaji, Kenji
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p. 1170 - 1176
(2007/10/02)
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- FACILE SYNTHESIS OF (E)-ALLYLIC ALCOHOLS BY ACID-CATALYZED MODIFICATION OF THE MISLOW-EVANS REARRANGEMENT OF ALLYLIC SULFOXIDES
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The Mislow-Evans rearrangement of α,β- and α,γ-disubstituted allylic sulfoxides (2) to (E)-allylic alcohols (4) was found to occur under acidic conditions.By combination of this method with a catalytic oxidation of allylic sulfides (1), a novel one-pot tr
- Masaki, Yukio,Sakuma, Kazuhiko,Kaji, Kenji
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p. 2531 - 2534
(2007/10/02)
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- Facile Regio- and Stereo-specific Allylic Oxidation of gem-Dimethyl Olefins via Addition of Benzenesulphenyl Chloride. Synthesis of Allylic Oxygenated Terpenes
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Novel and facile terminal trans-allylic and internal allylic oxidations of the gem-dimethyl olefin terminus of the terpenoids (1) are described which take place site-, regio-, and stereo-specificially via the same intermediate adduct between benzenesulphenyl chloride and (1).By this method, the allylic oxygenated terpenes (+/-)-nuciferal (11), (+/-)-ar-turmerone (12), (+/-)-ipsdienol (3c), neotorreyol (2e), (+/-)-6-hydroxydendrolasin (3e), and 6-oxodendrolasin (14) were synthesized.
- Masaki, Yukio,Hashimoto, Kinji,Sakuma, Kazuhiko,Kaji,Kenji
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p. 1289 - 1295
(2007/10/02)
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- FACILE FUNCTIONALIZATION OF THE ISOPROPYLIDENE TERMINUS OF ACYCLIC MONOTERPENES BY WAY OF BENZENESULFENYL CHLORIDE ADDITION
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Highly site- and regioselective terminal functionalizations of acyclic monoterpenes 1 via benzenesulfenyl chloride addition followed by hydrolysis assisted by silica gel, dehydrochlorination under neutral or weakly basic condition, or dehydrochlorination by strongly basic treatment respectively providing β-hydroxy sulfides 3, terminal methallylic sulfides 4, or vinylsulfides 5 are developed.Conversion of 4 to terminal trans-allylic alcohols 10 via sulfoxides 9 by the Evans procedure is also described.
- Masaki, Yukio,Hashimoto, Kinji,Kaji, Kenji
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p. 3481 - 3490
(2007/10/02)
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