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A Comparison Of The Benzylic And The Allylic Group As A Donor In The Formal [4+2] Cycloaddition To Tetrahydropyrans Using Donor-acceptor Cyclobutanes

A. Ahmed, S. Christie, G. Pritchard
Published 2017 · Chemistry

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The allyl group was shown to be preferred over the benzyl group as a donor in the formal [4+2]-cycloaddition reaction between a donor-acceptor cyclobutane and various aldehydes to give tetrahydropyrans.
This paper references
10.1039/B605329G
Preparation of highly substituted pyrrolidines via an organometallic dipole.
S. Christie (2006)
10.1248/CPB.60.21
Formal [4+2] cycloaddition of di-tert-butyl 2-ethoxycyclobutane-1,1-dicarboxylate with ketones or aldehydes and tandem lactonization.
Ryohei Okado (2012)
10.1016/S0040-4020(03)00244-8
Practical routes to diacetylenic ketones and their application for the preparation of alkynyl substituted pyridines, pyrimidines and pyrazoles
M. Adamo (2003)
10.1021/OL034736N
An unusual oxidative cyclization: studies towards the biomimetic synthesis of pyridomacrolidin.
Nageswara Rao Irlapati (2003)
Org
M.M.A.R. Moustafa (2012)
10.1021/ja8045684
Lewis acid-catalyzed intermolecular [4 + 2] cycloaddition of 3-alkoxycyclobutanones to aldehydes and ketones.
J. Matsuo (2008)
10.1039/c3cc44364g
A mild Lewis acid mediated epoxy-ester to bicyclic ortho ester rearrangement.
A. Ahmed (2013)
10.1016/J.TETLET.2011.11.067
Formal [4+2] cycloaddition of cyclobutanones bearing alkyne–cobalt complex at their 3-positions
M. Kawano (2012)
Chem
S.D.R. Christie (2009)
10.1021/ja906755e
Formal [4 + 2] cycloaddition of donor-acceptor cyclobutanes and aldehydes: stereoselective access to substituted tetrahydropyrans.
A. T. Parsons (2009)
Chem
A. Ahmed (2013)
10.1021/ol102062t
Ytterbium triflate catalyzed synthesis of alkoxy-substituted donor-acceptor cyclobutanes and their formal [4 + 2] cycloaddition with imines: stereoselective synthesis of piperidines.
M. M. A. R. Moustafa (2010)
and D
A. Ma (2008)
10.1039/A704526C
A versatile approach to pyrimidin-4-yl substituted α-aminoacids from alkynyl ketones; the total synthesis of l-lathyrine
R. Adlington (1997)
10.1021/OL026467R
Biomimetic cycloaddition approach to tropolone natural products via a tropolone ortho-quinone methide.
R. Adlington (2002)
10.1016/J.TETLET.2009.08.013
Formal [4+2] cycloaddition between 3-ethoxycyclobutanones and silyl enol ethers
J. Matsuo (2009)
Chem
A. T Parsons (2009)
10.1039/b917332c
Preparation of highly substituted tetrahydropyrans via a metal assisted dipolar cycloaddition reaction.
Eric A. Allart (2009)
10.1515/9783111548050-028
Q
Chlorpromazine Thorazine (1824)
10.1021/ol102063f
Formal [4 + 2] cycloaddition of alkoxy-substituted donor-acceptor cyclobutanes and aldehydes catalyzed by Yb(OTf)3.
M. M. A. R. Moustafa (2010)
10.1016/J.TETLET.2008.03.051
Enantioselective organocatalytic Michael addition of malonates to α,β-unsaturated aldehydes in water
A. Ma (2008)
10.1055/S-0028-1083282
Complementary Reactions of AllylicCarbamates Using Palladium(II): Formation of Oxazolidinonesor Allylic Amides from a Common Precursor
S. Christie (2009)
10.1021/ol1021355
Asymmetric synthesis of 2,3-dihydro-4-pyranones by reaction of chiral 3-alkoxycyclobutanone and aldehydes.
Shoko Negishi (2010)
10.1039/c2cc17200c
Thermo-sensitive imprinted polymer coating CdTe quantum dots for target protein specific recognition.
W. Zhang (2012)
10.1021/JO9712254
Synthetic and Mechanistic Studies of the Retro-Claisen Rearrangement. 3. A Route to Enantiomerically Pure Vinyl Cyclobutane Diesters via a Highly Diastereoselective Syn SN2‘ Reaction and Their Rearrangement to Enantiomerically Pure Dihydrooxacenes
R. K. Boeckman (1997)
10.1246/CL.1991.1149
Novel[4+2]-type reaction of 2-(dimethylamino)cyclobutanecarboxylic esters with carbonyl compounds
S. Shimada (1991)
Chem
E. A. Ellart (2009)
10.1016/S0040-4039(99)02263-7
Homologation of allylic alcohols. An approach to cyclic and acyclic polyoxygenated compounds
Ryan J Davoille (2000)
10.1039/B411367E
Novel formation and use of a Nicholas carbocation in the synthesis of highly substituted tetrahydrofurans.
S. Christie (2004)
Synlett, 2008, 2169; W
W. R. Bowman (1255)
10.1021/ol901329c
Tin(IV) chloride catalyzed cycloaddition reactions between 3-ethoxycyclobutanones and allylsilanes.
J. Matsuo (2009)
10.1021/ol202334s
A facile synthesis of substituted 2-alkylquinolines through [3+3] annulation between 3-ethoxycyclobutanones and aromatic amines at room temperature.
G. Shan (2011)
10.1016/S0960-894X(99)00690-3
Novel C-4 heteroaromatic kainoid analogues: a parallel synthesis approach.
J. Baldwin (2000)
10.1002/anie.201206734
Regioselective inter- and intramolecular formal [4+2] cycloaddition of cyclobutanones with indoles and total synthesis of (±)-aspidospermidine.
M. Kawano (2013)
Chem
S. Shimada (1149)
10.1021/OL0200504
Total synthesis of pyridovericin: studies toward the biomimetic synthesis of pyridomacrolidin.
J. Baldwin (2002)
10.1021/ol1012313
A new synthesis of 2,3-di- or 2,3,3-trisubstituted 2,3-dihydro-4-pyridones by reaction of 3-ethoxycyclobutanones and N-p-toluenesulfonyl imines using titanium(IV) chloride: synthesis of (+/-)-bremazocine.
J. Matsuo (2010)
10.1021/ol200220d
The formal [4+3] cycloaddition between donor-acceptor cyclobutanes and nitrones.
A. C. Stevens (2011)
10.1055/S-0028-1087516
Formation of PolysubstitutedTetrahydrofurans on an Iron Tricarbonyl η5-PentadienylTemplate
S. Christie (2009)
10.1016/J.TET.2006.01.090
Studies towards the biomimetic synthesis of pyridomacrolidin
Nageswara Rao Irlapati (2006)



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