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Literature DB >> 27376747

Ring opening of epoxides with C-nucleophiles.

Abstract

Ring opening of epoxides has been an area of interest for organic chemists, owing to their reactivity toward nucleophiles. Such reactions yield important products depending on the type of nucleophiles used. This review article covers the synthetic approaches (1991-2015) used for the ring opening of epoxides via carbon nucleophiles.

Entities: Chemical

Keywords: C-Nucleophiles; Dithianes; Enolates; Epoxides; Ring opening reactions

Mesh：

Substances：

Year: 2016 PMID： 27376747 DOI： 10.1007/s11030-016-9686-7

Source DB: PubMed Journal: Mol Divers ISSN： 1381-1991 Impact factor: 2.943

10 in total

1. Atom economic asymmetric creation of quaternary carbon: regio- and enantioselective reactions of a vinylepoxide with a carbon nucleophile.

Authors: B M Trost; C Jiang
Journal: J Am Chem Soc Date: 2001-12-26 Impact factor: 15.419

2. Control of olefin geometry in the bryostatin B-ring through exploitation of a C(2)-symmetry breaking tactic and a Smith-Tietze coupling reaction.

Authors: K J Hale; M G Hummersone; G S Bhatia
Journal: Org Lett Date: 2000-07-27 Impact factor: 6.005

3. Multicomponent linchpin couplings of silyl dithianes: synthesis of the Schreiber C(16-28) trisacetonide subtarget for mycoticins A and B.

Authors: A B Smith; S M Pitram
Journal: Org Lett Date: 1999-12-16 Impact factor: 6.005

4. Dithiane additions to vinyl epoxides: steric control over the SN2 and SN2' manifolds.

Authors: Amos B Smith; Suresh M Pitram; Matthew J Gaunt; Sergey A Kozmin
Journal: J Am Chem Soc Date: 2002-12-11 Impact factor: 15.419

Review 5. The development of endo-selective epoxide-opening cascades in water.

Authors: Christopher J Morten; Jeffery A Byers; Aaron R Van Dyke; Ivan Vilotijevic; Timothy F Jamison
Journal: Chem Soc Rev Date: 2009-09-16 Impact factor: 54.564

6. Synthesis of the core structure of apicularen a by transannular cyclization.

Authors: Sven M Kühnert; Martin E Maier
Journal: Org Lett Date: 2002-02-21 Impact factor: 6.005

7. Mild, fast, and stereoselective epoxide opening by ketone enolate anions. Application to synthesis of the norlignan curculigine.

Authors: Gary H Posner; John P Maxwell; Mehmet Kahraman
Journal: J Org Chem Date: 2003-04-18 Impact factor: 4.354

8. A direct method for the conversion of terminal epoxides into gamma-butanolides.

Authors: Mohammad Movassaghi; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2002-03-20 Impact factor: 15.419

9. Alkenes from terminal epoxides using lithium 2,2,6,6-tetramethylpiperidide and organolithiums or grignard reagents.

Authors: David M Hodgson; Matthew J Fleming; Steven J Stanway
Journal: J Am Chem Soc Date: 2004-10-06 Impact factor: 15.419

Review 10. Epoxide-opening cascades in the synthesis of polycyclic polyether natural products.

Authors: Ivan Vilotijevic; Timothy F Jamison
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336