+ Site Statistics
References:
54,258,434
Abstracts:
29,560,870
PMIDs:
28,072,757
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Asymmetric synthesis of bicyclic dihydropyrans via organocatalytic inverse-electron-demand oxo-Diels-Alder reactions of enolizable aliphatic aldehydes



Asymmetric synthesis of bicyclic dihydropyrans via organocatalytic inverse-electron-demand oxo-Diels-Alder reactions of enolizable aliphatic aldehydes



Chemical Communications 52(70): 10617-10620



A highly enantioselective organocatalytic inverse-electron-demand oxo-Diels-Alder reaction involving aqueous acetaldehyde has been discovered. The reaction, in which cyclic enones serve as dienes in the presence of readily available secondary amine catalysts, allows facile construction of optically active bicyclic dihydropyrans. Other typical enolizable aliphatic aldehydes can also serve as competent dienophiles in the reaction.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 057261172

Download citation: RISBibTeXText

PMID: 27436351

DOI: 10.1039/c6cc05001h


Related references

Organocatalytic asymmetric inverse-electron-demand aza-Diels-Alder reaction of N-sulfonyl-1-aza-1,3-butadienes and aldehydes. Angewandte Chemie 47(51): 9971-9974, 2008

Asymmetric inverse-electron-demand hetero-Diels-Alder reaction for the construction of bicyclic skeletons with multiple stereocenters by using a bifunctional organocatalytic strategy: an efficient approach to chiral macrolides. Chemistry 18(36): 11465-11473, 2012

Asymmetric Diels-Alder and inverse-electron-demand hetero-Diels-Alder reactions of β,γ-unsaturated α-ketoesters with cyclopentadiene catalyzed by N,N'-dioxide copper(II) complex. Chemistry 16(39): 11963-8, 2010

Organocatalytic asymmetric inverse-electron-demand Diels-Alder reaction of electron-deficient dienes and crotonaldehyde. Angewandte Chemie 49(36): 6418-6420, 2010

Organocatalytic regio- and stereoselective inverse-electron-demand aza-Diels-Alder reaction of alpha,beta-unsaturated aldehydes and N-tosyl-1-aza-1,3-butadienes. Angewandte Chemie 48(30): 5474-5477, 2009

Organocatalyzed Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reaction of α,β-Unsaturated Trifluoromethyl Ketones and Aldehydes. Synlett 2008(7): 1017-1020, 2008

β,γ-Regioselective inverse-electron-demand aza-Diels-Alder reactions with α,β-unsaturated aldehydes via dienamine catalysis. Organic Letters 16(15): 3986-3989, 2014

Catalytic Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reactions. Chemical Record 17(12): 1184-1202, 2017

Highly enantioselective inverse-electron-demand hetero-diels-alder reactions of alpha,beta-unsaturated aldehydes. Angewandte Chemie 41(16): 3059-3061, 2002

Bifunctional organocatalytic strategy for inverse-electron-demand Diels-Alder reactions: highly efficient in situ substrate generation and activation to construct azaspirocyclic skeletons. Angewandte Chemie 51(9): 2084-2087, 2012

Asymmetric diels alder reactions inverse electron demand reactions of esters of 3 hydroxypyran 2 one with vinyl ethers use of high pressure to avoid decarboxylation of adducts. Tetrahedron Letters 32(27): 3147-3150, 1991

Inverse-Electron-Demand Diels-Alder Reactions for the Synthesis of Pyridazines on DNA. Organic Letters: -, 2018

Synthesis and inverse electron demand Diels-Alder reactions of 3,6-bis(3,4-dimethoxybenzoyl)-1,2,4,5-tetrazine. Journal of Organic Chemistry 68(9): 3593-3598, 2003

First asymmetric synthesis of quinoline derivatives by inverse electron demand (IED) Diels-Alder reaction using chiral Ti(IV) complex. Organic Letters 3(13): 1973-1976, 2001

The first organocatalytic enantioselective inverse-electron-demand hetero-Diels-Alder reaction. Angewandte Chemie 42(13): 1498-1501, 2003