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Literature DB >> 16986946

Stereoselective epoxidation of 4-deoxypentenosides: a polarized-pi model.

Gang Cheng¹, Fabien P Boulineau, Siong-Tern Liew, Qicun Shi, Paul G Wenthold, Alexander Wei.

Abstract

The high facioselectivity in the epoxidation of 4-deoxypentenosides (4-DPs) by dimethyldioxirane (DMDO) correlates with a stereoelectronic bias in the 4-DPs' ground-state conformations, as elucidated by polarized-pi frontier molecular orbital (PPFMO) analysis.

Entities: Chemical

Mesh：

Substances：
Alkenes
Epoxy Compounds

Year: 2006 PMID： 16986946 PMCID： PMC2596068 DOI： 10.1021/ol0617401

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

7 in total

1. Using perturbation and frontier molecular orbital theory to predict diastereofacial selectivity.

Authors: J J Dannenberg
Journal: Chem Rev Date: 1999-05-12 Impact factor: 60.622

2. CH.O Hydrogen Bonding Influences pi-Facial Stereoselective Epoxidations We are grateful to the National Institute of General Medical Sciences, National Institutes of Health (GM-36700) for financial support of this research and the National Computational Science Alliance (Illinois) for computer time and support.

Authors: Ilyas Washington; K. N. Houk
Journal: Angew Chem Int Ed Engl Date: 2001-12-03 Impact factor: 15.336

Review 3. Synthesis and reactions of unsaturated sugars.

Authors: Robert J Ferrier; John O Hoberg
Journal: Adv Carbohydr Chem Biochem Date: 2003 Impact factor: 12.200

4. Theory and modeling of stereoselective organic reactions.

Authors: K N Houk; M N Paddon-Row; N G Rondan; Y D Wu; F K Brown; D C Spellmeyer; J T Metz; Y Li; R J Loncharich
Journal: Science Date: 1986-03-07 Impact factor: 47.728

5. Substituent dependence of the diastereofacial selectivity in iodination and bromination of glycals and related cyclic enol ethers.

Authors: A Boschi; C Chiappe; A De Rubertis; M F Ruasse
Journal: J Org Chem Date: 2000-12-15 Impact factor: 4.354

6. Mirror-image carbohydrates: synthesis of the unnatural enantiomer of a blood group trisaccharide.

Authors: Fabien P Boulineau; Alexander Wei
Journal: J Org Chem Date: 2004-05-14 Impact factor: 4.354

7. Synthesis of L-sugars from 4-deoxypentenosides.

Authors: Fabien P Boulineau; Alexander Wei
Journal: Org Lett Date: 2002-06-27 Impact factor: 6.005

7 in total

5 in total

Stereoselective epoxidation of 4-deoxypentenosides: a polarized-pi model.

1. Using perturbation and frontier molecular orbital theory to predict diastereofacial selectivity.

Review 3. Synthesis and reactions of unsaturated sugars.

4. Theory and modeling of stereoselective organic reactions.

5. Substituent dependence of the diastereofacial selectivity in iodination and bromination of glycals and related cyclic enol ethers.

6. Mirror-image carbohydrates: synthesis of the unnatural enantiomer of a blood group trisaccharide.

7. Synthesis of L-sugars from 4-deoxypentenosides.

1. Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides.

2. syn additions to 4alpha-epoxypyranosides: synthesis of L-idopyranosides.

3. Synthesis and reactivity of 4'-deoxypentenosyl disaccharides.

4. Turning Spiroketals Inside Out: A Rearrangement Triggered by an Enol Ether Epoxidation.

5. Glycosyl dithiocarbamates: β-selective couplings without auxiliary groups.