Literature DB >> 22900546

Mechanism of the regio- and diastereoselective ring expansion reaction using trimethylsilyldiazomethane.

Takeo Sakai1, Satoshi Ito, Hiroki Furuta, Yuki Kawahara, Yuji Mori.   

Abstract

An equatorial attack of TMS-diazomethane was determined to be the first step of the BF(3)-promoted ring expansion reaction of six-membered ketones using TMS-diazomethane. The migration reaction occurred in a conformation in which the carbonyl oxygen and the TMS group were antiperiplanar to predominantly afford trans-seven-membered ketones.

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Year:  2012        PMID: 22900546     DOI: 10.1021/ol302032w

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


  1 in total

1.  A total synthesis of (-)-Hortonone C.

Authors:  Doleshwar Niroula; Liam P Hallada; Snezna Rogelj; Rodolfo Tello-Aburto
Journal:  Tetrahedron       Date:  2016-12-11       Impact factor: 2.457

  1 in total

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