Literature DB >> 16839134

New approaches to polysubstituted pyrroles and gamma-lactams based on nucleophilic addition of Ti(IV) enolates derived from alpha-diazo-beta-keto carbonyl compounds to N-tosylimines.

Changqing Dong1, Guisheng Deng, Jianbo Wang.   

Abstract

The Ti(IV) enolates derived from alpha-diazo-beta-keto esters or ketones efficiently add to TiCl4-activated N-tosylimines to give delta-N-tosylamino substituted alpha-diazo-beta-keto carbonyl compounds. The diazo decomposition of the addition products occurs under Rh2(OAc)4-catalyzed or photoinduced conditions to afford pyrrole or gamma-lactam derivatives, both in high yields.

Entities:  

Year:  2006        PMID： 16839134     DOI： 10.1021/jo0605039

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  5 in total

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Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

2.  Toward a total synthesis of the stemofoline alkaloids: Advancement of a 1,3-dipolar cycloaddition strategy.

Authors:  Charles S Shanahan; Nathan O Fuller; Bjoern Ludolph; Stephen F Martin
Journal:  Tetrahedron Lett       Date:  2011-08-10       Impact factor: 2.415

3.  Synthesis of polysubstituted pyrroles from sulfinimines (N-sulfinyl imines).

Authors:  Franklin A Davis; Kerisha A Bowen; He Xu; Venkata Velvadapu
Journal:  Tetrahedron       Date:  2008-05-05       Impact factor: 2.457

4.  Azirinium ylides from α-diazoketones and 2H-azirines on the route to 2H-1,4-oxazines: three-membered ring opening vs 1,5-cyclization.

Authors:  Nikolai V Rostovskii; Mikhail S Novikov; Alexander F Khlebnikov; Galina L Starova; Margarita S Avdontseva
Journal:  Beilstein J Org Chem       Date:  2015-03-02       Impact factor: 2.883

5.  Copper-catalyzed condensation of imines and α-diazo-β-dicarbonyl compounds: modular and regiocontrolled synthesis of multisubstituted pyrroles.

Authors:  Wei Wen Tan; Naohiko Yoshikai
Journal:  Chem Sci       Date:  2015-08-03       Impact factor: 9.825
  5 in total

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