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Organocatalytic Enantioselective Michael Addition Of Cyclic Hemiacetals To Nitroolefins: A Facile Access To Chiral Substituted 5- And 6-membered Cyclic Ethers.

Yadong Zhu, P. Qian, Jiyang Yang, S. Chen, Yanwei Hu, Ping Wu, Weiqi Wang, Wei Zhang, Shilei Zhang
Published 2015 · Chemistry, Medicine

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An efficient aminocatalytic enantioselective Michael addition of readily available cyclic hemiacetals to nitroolefins has been developed. The strategy serves as a powerful approach to synthetically valuable chiral 3-substituted tetrahydrofurans (THFs) and tetrahydropyrans (THPs). The synthetic utilities of the versatile Michael adducts also have been demonstrated in the synthesis of 2,3-disubstituted cyclic ethers, α-substituted lactones and venlafaxine analogues.
This paper references
10.1021/cr3004778
Tetrahydrofuran-containing macrolides: a fascinating gift from the deep sea.
A. Lorente (2013)
10.1002/chem.200800788
Organocatalytic enantioselective synthesis of highly functionalized polysubstituted pyrrolidines.
Nerea Ruiz (2008)
10.1093/nar/gkt1247
ASD v2.0: updated content and novel features focusing on allosteric regulation
Z. Huang (2014)
10.1016/0040-4020(96)00705-3
Synthetic studies on prehispanolone and 14,15-dihydroprehispanolone
E. S. Wang (1996)
10.1021/CR068373R
Small-molecule H-bond donors in asymmetric catalysis.
A. G. Doyle (2007)
10.1039/B500186M
Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action.
A. Bermejo (2005)
10.1021/CR010374Q
Palladium-assisted routes to nucleosides.
L. Agrofoglio (2003)
10.1016/J.TET.2006.03.116
Nickel-catalyzed multi-component connection reaction of isoprene, aldimines (lactamines), and diphenylzinc
K. Kojima (2006)
10.1021/CR068372Z
Organocatalysis by N-heterocyclic carbenes.
D. Enders (2007)
10.1039/B514045P
An update on bioactive plant lignans.
M. Saleem (2005)
10.1021/CR068402Y
Chalcogenides as organocatalysts.
E. M. McGarrigle (2007)
10.1002/1099-0690(200012)2000:23<3893::AID-EJOC3893>3.0.CO;2-E
On the Stereoselectivity of γ‐Lactol Substitutions with Allyl‐ and Propargylsilanes − Synthesis of Disubstituted Tetrahydrofuran Derivatives
A. Schmitt (2000)
10.1002/ANIE.200500599
Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes.
Y. Hayashi (2005)
10.1002/chem.201103015
An amine-catalyzed enantioselective [3+2] cycloaddition of azomethine ylides and α,β-unsaturated aldehydes: applications and mechanistic implications.
Silvia Reboredo (2012)
10.1002/ANIE.200704161
Highly efficient catalytic system for enantioselective Michael addition of aldehydes to nitroalkenes in water.
S. Zhu (2008)
10.1021/ja501568k
Immobilized bisdiazaphospholane catalysts for asymmetric hydroformylation.
Tyler T. Adint (2014)
10.1021/CR040614C
Advances in the total synthesis of biologically important marine macrolides.
K. Yeung (2005)
10.1021/ol801772p
Enantioselective organocatalytic conjugate addition of aldehydes to nitrodienes.
Sébastien Belot (2008)
10.1002/anie.200800847
Catalytic asymmetric Michael reactions of acetaldehyde.
P. García-García (2008)
10.1021/cr9002165
C-nucleosides: synthetic strategies and biological applications.
J. Štambaský (2009)
10.1021/CR040629A
Total synthesis of oxacyclic macrodiolide natural products.
E. J. Kang (2005)
10.1021/CR0684016
Asymmetric enamine catalysis.
S. Mukherjee (2007)
10.1021/ol8023133
Sequential organocatalyzed Michael addition/[3 + 2]-heterocyclization for the stereoselective synthesis of fused-isoxazoline precursors of enantiopure cyclopentanoids.
D. Bonne (2008)
10.1021/ol400963d
Asymmetric cross-dimerization between methyl methacrylate and substituted alkene by Ru(0)-bicyclononadiene complex.
Yuki Hiroi (2013)
10.1021/jo200838v
Thiourea/proline derivative-catalyzed synthesis of tetrahydrofuran derivatives: a mechanistic view.
Suzanne M. Opalka (2011)
10.1016/J.TETASY.2009.10.034
Diastereoselective synthesis of 2,5-disubstituted tetrahydrofurans
Gaël Jalce (2009)
10.1002/1099-0690(200103)2001:6<1169::AID-EJOC1169>3.0.CO;2-L
Lewis Acid‐Promoted Reactions of γ‐Lactols with Silyl Enol Ethers — Stereoselective Formation of Functionalized Tetrahydrofuran Derivatives
A. Schmitt (2001)
10.1002/ANIE.200461959
Direct, highly enantioselective pyrrolidine sulfonamide catalyzed Michael addition of aldehydes to nitrostyrenes.
Wei Wang (2005)
10.1021/ja800345r
Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids.
Yonggui Chi (2008)
10.1021/CR000446Y
Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides, and C-nucleosides.
M. Ferrero (2000)
10.1021/CR940210S
Strategy and methodology development for the total synthesis of polyether ionophore antibiotics.
M. Faul (2000)
10.1021/CR0683764
Recent developments in the use of catalytic asymmetric ammonium enolates in chemical synthesis.
M. Gaunt (2007)
10.1016/J.TET.2006.08.105
Recent Advances in the Stereoselective Synthesis of Tetrahydrofurans.
J. Wolfe (2007)
10.1002/anie.200901333
Enantioselective organocatalytic domino oxa-Michael/aldol/hemiacetalization: synthesis of polysubstituted furofuranes containing four stereocenters.
E. Reyes (2009)
10.1002/chem.200800145
Organocatalytic multicomponent alpha-methylenation/Diels-Alder reactions: a versatile route to substituted cyclohexenecarbaldehyde derivatives.
Yue Zou (2008)



This paper is referenced by
10.1021/acs.orglett.6b00160
Substrate-Controlled, One-Pot Synthesis: Access to Chiral Chroman-2-one and Polycyclic Derivatives.
Xue-li Sun (2016)
10.1039/c6ob00953k
From racemic precursors to fully stereocontrolled products: one-pot synthesis of chiral α-amino lactones and lactams.
Zhi-Hao You (2016)
10.1002/CHIN.201534021
Organocatalytic Enantioselective Michael Addition of Cyclic Hemiacetals to Nitroolefins: A Facile Access to Chiral Substituted 5- and 6-Membered Cyclic Ethers.
Yadong Zhu (2015)
10.1002/9781119125082.CH10
Addition Reactions: Polar Additions
A. C. Knipe (2019)
10.3390/molecules22060895
Recent Advances in Asymmetric Organocatalyzed Conjugate Additions to Nitroalkenes
D. Alonso (2017)
10.1002/0471264180.OR090.01
The Catalytic, Enantioselective Michael Reaction
E. Reyes (2016)
10.1002/adsc.202000100
Aldehydes Switch Regioselectivity: a Prins Cyclization Strategy for the Synthesis of Indoline‐fused THFs and Indole‐fused Oxepanes
X. Chen (2020)
10.1016/J.TET.2016.07.067
Stereoselective reactions of nitro compounds in the synthesis of natural compound analogs and active pharmaceutical ingredients
A. Sukhorukov (2016)
10.1002/ADSC.201601335
Asymmetric Organocatalytic Synthesis of Benzopyran‐ and Benzofuran‐Fused Polycyclic Acetals
Jiyang Yang (2017)
10.1002/ADSC.201801676
The Employment of Sodium Hydride as a Michael Donor in Palladium‐catalyzed Reductions of α, β‐Unsaturated Carbonyl Compounds
L. Ye (2019)
10.1039/c5ob02571k
One-pot, highly efficient, asymmetric synthesis of ring-fused piperidine derivatives bearing N,O- or N,N-acetal moieties.
J. Li (2016)
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