Literature DB >> 20426398

A facile, one-pot synthesis of beta-substituted (Z)-acrylonitriles utilizing an alpha-diaminoboryl carbanion.

Takashi Tomioka1, Yusuke Takahashi, Trey G Vaughan, Takayoshi Yanase.   

Abstract

A simple three-step single-pot procedure for Z-stereoselective synthesis of beta-monosubstituted acrylonitriles has been established. The reaction involves olefination of aldehydes with an in situ generated alpha-diaminoboryl carbanion species. Various aromatic and aliphatic aldehydes were smoothly converted into the corresponding (Z)-olefin products (up to 96:4 ratio) in good yields (80-98%).

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Year:  2010        PMID: 20426398     DOI: 10.1021/ol100534s

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


  1 in total

1.  Reactions of an anionic chelate phosphane/borata-alkene ligand with [Rh(nbd)Cl]2, [Rh(CO)2Cl]2 and [Ir(cod)Cl]2.

Authors:  Kohei Watanabe; Atsushi Ueno; Xin Tao; Karel Škoch; Xiaoming Jie; Sergei Vagin; Bernhard Rieger; Constantin G Daniliuc; Matthias C Letzel; Gerald Kehr; Gerhard Erker
Journal:  Chem Sci       Date:  2020-06-19       Impact factor: 9.825

  1 in total

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