Literature DB >> 18958293

Stereoselective Synthesis of trans-Olefins by the Copper-Mediated S(N)2' Reaction of Vinyl Oxazines with Grignard Reagents. Asymmetric Synthesis of D-threo-Sphingosines.

Om V Singh1, Hyunsoo Han.   

Abstract

The S(N)2' reaction of 6-vinyl-5,6-dihydro-4H-[1,3]oxazines with Grignard reagents in the presence of CuCN was studied, and high trans selectivity for the formation of double bond was observed with a variety of RMgX. The S(N)2' reaction, coupled with regioselective asymmetric aminohydroxylation reaction, provided a highly efficient route for the asymmetric synthesis of D-threo-N-acetylsphingosine.

Entities:  

Year:  2007        PMID： 18958293      PMCID： PMC2572814          DOI： 10.1016/j.tetlet.2007.01.145

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  13 in total

1.  Highly Enantioselective Regiodivergent and Catalytic Parallel Kinetic Resolution This work was supported by the Ministero dell'Università e della Ricerca Scientifica e Tecnologica (MURST, Roma) and by the University of Pisa. We gratefully acknowledge Merck for the generous financial support derived from the 2000 ADP Chemistry Award.

Authors:  Fabio Bertozzi; Paolo Crotti; Franco Macchia; Mauro Pineschi; Ben L. Feringa
Journal:  Angew Chem Int Ed Engl       Date:  2001-03-02       Impact factor: 15.336

2.  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

3.  Diastereoselective synthesis of psi[(E)-CMe=CH]- and psi[(E)-CMe=CMe]- type dipeptide isosteres based on organocopper-mediated anti-S(N)2' reaction.

Authors:  Shinya Oishi; Ayumu Niida; Takae Kamano; Yoshihiko Odagaki; Hirokazu Tamamura; Akira Otaka; Nobuyuki Hamanaka; Nobutaka Fujii
Journal:  Org Lett       Date:  2002-04-04       Impact factor: 6.005

4.  A practical synthesis of D-erythro-sphingosine using a cross-metathesis approach.

Authors:  Staffan Torssell; Peter Somfai
Journal:  Org Biomol Chem       Date:  2004-04-20       Impact factor: 3.876

5.  Hydrogen bond directed highly regioselective palladium-catalyzed allylic substitution.

Authors:  Gregory R Cook; Hui Yu; S Sankaranarayanan; P Sathya Shanker
Journal:  J Am Chem Soc       Date:  2003-04-30       Impact factor: 15.419

6.  An efficient synthesis of D-erythro- and D-threo-sphingosine from D-glucose: olefin cross-metathesis approach.

Authors:  Vinod D Chaudhari; K S Ajish Kumar; Dilip D Dhavale
Journal:  Org Lett       Date:  2005-12-22       Impact factor: 6.005

7.  Chiral alpha-substituted carbonyls and alcohols from the S(N)2' displacement of cuprates on chiral carbonates: An alternative to the alkylation of chiral enolates

Authors: 
Journal:  J Org Chem       Date:  2000-10-20       Impact factor: 4.354

Review 8.  Aziridines: epoxides' ugly cousins?

Authors:  J B Sweeney
Journal:  Chem Soc Rev       Date:  2002-09       Impact factor: 54.564

9.  Regio- and stereoselective synthesis of (E)-alkene trans-Xaa-Pro dipeptide mimetics utilizing organocopper-mediated anti-S(N)2' reactions.

Authors:  Akira Otaka; Fumihiko Katagiri; Takayoshi Kinoshita; Yoshihiko Odagaki; Shinya Oishi; Hirokazu Tamamura; Nobuyuki Hamanaka; Nobutaka Fujii
Journal:  J Org Chem       Date:  2002-08-23       Impact factor: 4.354

10.  Multicomponent linchpin couplings. Reaction of dithiane anions with terminal epoxides, epichlorohydrin, and vinyl epoxides: efficient, rapid, and stereocontrolled assembly of advanced fragments for complex molecule synthesis.

Authors:  Amos B Smith; Suresh M Pitram; Armen M Boldi; Matthew J Gaunt; Chris Sfouggatakis; William H Moser
Journal:  J Am Chem Soc       Date:  2003-11-26       Impact factor: 15.419
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