Formal [3 + 2] Cycloaddition Reaction of [1,4]Oxazin-2-ones and α-Alkynyl Ketones via a Tandem Mukaiyama-Aldol Addition/Aza-Cope Rearrangement

1999 ◽  
Vol 64 (18) ◽  
pp. 6891-6895 ◽  
Author(s):  
Daniel Obrecht ◽  
Cornelia Zumbrunn ◽  
Klaus Müller
Keyword(s):  
Cycloaddition Reaction ◽  
Cope Rearrangement ◽  
Mukaiyama Aldol ◽  
Aldol Addition

Aromatic aldehyde-selective aldol addition with aldehyde-derived silyl enol ethers

2018 ◽  
Vol 54 (4) ◽  
pp. 374-377 ◽  
Author(s):  
Takahiro Kawajiri ◽  
Reiya Ohta ◽  
Hiromichi Fujioka ◽  
Hironao Sajiki ◽  
Yoshinari Sawama
Keyword(s):  
Aromatic Aldehyde ◽  
Aldol Reaction ◽  
Aliphatic Aldehydes ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Mukaiyama Aldol Reaction ◽  
Mukaiyama Aldol ◽  
Aldol Addition

Unprecedented chemoselectivity between aromatic and aliphatic aldehydes has been achieved in the Mukaiyama aldol reaction using aldehyde-derived silyl enol ethers.

ChemInform Abstract: A Rapid Injection NMR Study of the Chelation Controlled Mukaiyama Aldol Addition: TiCl4 versus LiClO4 as the Lewis Acid.

ChemInform ◽  
2010 ◽  
Vol 23 (43) ◽  
pp. no-no
Author(s):  
M. T. REETZ ◽  
B. RAGUSE ◽  
C. F. MARTH ◽  
H. M. HUEGEL ◽  
T. BACH ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Nmr Study ◽  
Rapid Injection ◽  
Mukaiyama Aldol ◽  
Aldol Addition

A Chemoenzymatic Synthesis of the cis-Decalin Core Associated with the Novel Anti-Mitotic Agent Phomopsidin: Some Observations Concerning a High-Pressure-Promoted Diels–Alder Cycloaddition Reaction of (1S,2R)-3-Methyl-cis-1,2-dihydrocatechol and the Anionic Oxy–Cope Rearrangement of Compounds Derived from the Adduct

2004 ◽  
Vol 57 (7) ◽  
pp. 641 ◽  
Author(s):  
Martin G. Banwell ◽  
Alison J. Edwards ◽  
Malcolm D. McLeod ◽  
Scott G. Stewart
Keyword(s):  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Chemoenzymatic Synthesis ◽  
Cope Rearrangement ◽  
The Novel ◽  
X Ray Diffraction ◽  
Enantiomerically Pure ◽  
X Ray ◽  
Wittig Rearrangements ◽  
Rearrangement Reaction

The enantiomerically pure and enzymatically derived cis-1,2-dihydrocatechol 2 engages in a diastereofacially selective Diels–Alder cycloaddition reaction with commercially available lactone 3 at 19 kbar to afford adduct 4, which is readily elaborated to the diene-ol 13. Treatment of this last compound with KH/18[crown]-6 resulted in successive anionic oxy-Cope and 1,2-Wittig rearrangements to afford acyloin 14 embodying the cis-decalin core associated with the natural product phomopsidin (1). Compound 16 also engages in an anionic oxy-Cope rearrangement reaction to give, depending on the molar equivalents of base used, either the cis-decalin 17 or the hexahydroindene 18. The structure of compound 18 has been established by single-crystal X-ray diffraction analysis.

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