Literature DB >> 10880222

Diastereotopic differentiation on phosphorus templates via the ring-closing metathesis reaction.

D S Stoianova1, P R Hanson.   

Abstract

[reaction: see text] A strategy is described in which the ring-closing metathesis reaction is utilized to desymmetrize a number of pseudo-C(2)-symmetric phosphorus templates 1-3. These reactions give excellent levels of selectivity (12-15:1) with vinyl phosphonamides containing a (E)-Ph group on the diastereotopic olefins. This approach is being developed as an effective method of obtaining P-chiral phosphonamides and phosphonates.

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Year:  2000        PMID: 10880222     DOI: 10.1021/ol005952o

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


  5 in total

1.  Diastereoselective temporary silicon-tethered ring-closing-metathesis reactions with prochiral alcohols: a new approach to long-range asymmetric induction.

Authors:  P Andrew Evans; Jian Cui; Gerald P Buffone
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-17       Impact factor: 15.336

2.  Phosphate Tether-Mediated Ring-Closing Metathesis for the Generation of Medium to Large, P-Stereogenic Bicyclo[n.3.1]phosphates.

Authors:  Soma Maitra; Jana L Markley; Rambabu Chegondi; Paul R Hanson
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

3.  Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles.

Authors:  Wen-Jian Qian; Jung-Eun Park; Robert Grant; Christopher C Lai; James A Kelley; Michael B Yaffe; Kyung S Lee; Terrence R Burke
Journal:  Biopolymers       Date:  2015-11       Impact factor: 2.505

4.  Temporary Protection of H-Phosphinic Acids as a Synthetic Strategy.

Authors:  Laëtitia Coudray; Jean-Luc Montchamp
Journal:  European J Org Chem       Date:  2009-09

Review 5.  Synthetic strategies for the preparation of γ-phostams: 1,2-azaphospholidine 2-oxides and 1,2-azaphospholine 2-oxides.

Authors:  Jiaxi Xu
Journal:  Beilstein J Org Chem       Date:  2022-07-22       Impact factor: 2.544

  5 in total

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