Literature DB >> 14961626

Stereoselective carbon-carbon bond formation via the Mitsunobu displacement of chiral secondary benzylic alcohols.

Michael C Hillier1, Jean-Nicolas Desrosiers, Jean-François Marcoux, Edward J J Grabowski.   

Abstract

[reaction: see text] The stereoselective displacement of a variety of chiral benzylic alcohols with triethylmethanetricarboxylate (TEMT) under Mitsunobu conditions (DEAD, PMe(3)) has been demonstrated to proceed in good yield (70-94%) and with a high degree of inversion. Subsequent saponification and decarboxylation of the products thus obtained provide chiral 3-aryl-3-substituted propanoic acids without racemization.

Entities:  

Year:  2004        PMID： 14961626     DOI： 10.1021/ol036380l

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


  4 in total

1.  Stereoselective bioreduction of 1-(4-methoxyphenyl)ethanone by whole cells of marine-derived fungi.

Authors:  Lenilson C Rocha; Hercules V Ferreira; Rodrigo F Luiz; Lara D Sette; André L M Porto
Journal:  Mar Biotechnol (NY)       Date:  2011-12-13       Impact factor: 3.619

2.  Total Synthesis of (-)-Kopsifoline A and (+)-Kopsifoline E.

Authors:  In-Soo Myeong; Nadide Hazal Avci; Mohammad Movassaghi
Journal:  Org Lett       Date:  2021-11-12       Impact factor: 6.072

3.  Markedly improving asymmetric oxidation of 1-(4-methoxyphenyl) ethanol with Acetobacter sp. CCTCC M209061 cells by adding deep eutectic solvent in a two-phase system.

Authors:  Ping Wei; Jing Liang; Jing Cheng; Min-Hua Zong; Wen-Yong Lou
Journal:  Microb Cell Fact       Date:  2016-01-13       Impact factor: 5.328

4.  Asymmetric Synthesis of Second-Generation Light-Driven Molecular Motors.

Authors:  Thomas van Leeuwen; Wojciech Danowski; Edwin Otten; Sander J Wezenberg; Ben L Feringa
Journal:  J Org Chem       Date:  2017-05-01       Impact factor: 4.354
  4 in total

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