Literature DB >> 26067720

The β-Silyl Effect on the Memory of Chirality in Friedel-Crafts Alkylation Using Chiral α-Aryl Alcohols.

Toshiki Nokami, Yu Yamane, Shunsuke Oshitani, Jun-ka Kobayashi, Shin-ichiro Matsui, Takashi Nishihara, Hidemitsu Uno1, Shuichi Hayase, Toshiyuki Itoh.   

Abstract

Iron salt-catalyzed Friedel-Crafts alkylation of chiral α-aryl alcohols with a trimethylsilyl group was found to proceed with retention of the configuration of the hydroxyl group as a leaving group. The memory of chirality of this system stems from the β-silyl effect of the trimethylsilyl group on the carbocation intermediate.

Entities:  

Year:  2015        PMID: 26067720     DOI: 10.1021/acs.orglett.5b01582

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


  2 in total

1.  Mechanistic insights on the Pd-catalyzed addition of C-X bonds across alkynes - a combined experimental and computational study.

Authors:  Theresa Sperger; Christine M Le; Mark Lautens; Franziska Schoenebeck
Journal:  Chem Sci       Date:  2017-01-27       Impact factor: 9.825

2.  Memory of Chirality as a Prominent Pathway for the Synthesis of Natural Products through Chiral Intermediates.

Authors:  Tomas Hardwick; Nisar Ahmed
Journal:  ChemistryOpen       Date:  2018-06-19       Impact factor: 2.911

  2 in total

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