Literature DB >> 18396885

Picolinoxy group, a new leaving group for anti SN2' selective allylic substitution with aryl anions based on Grignard reagents.

Yohei Kiyotsuka1, Hukum P Acharya, Yuji Katayama, Tomonori Hyodo, Yuichi Kobayashi.   

Abstract

The picolinoxy group was found to be an extremely powerful leaving group for allylic substitution with aryl nucleophiles derived from ArMgBr and CuBr*Me2S. The substitution proceeds with anti SN2' pathway and with high chirality transfer. The electron-withdrawing effect of the pyridyl group and chelation to MgBr2 are likely the origin of success. Results suggesting these effects were obtained.

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Year:  2008        PMID： 18396885     DOI： 10.1021/ol800300x

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


  3 in total

1.  Ruthenium-Catalyzed C-H Allylation of Alkenes with Allyl Alcohols via C-H Bond Activation in Aqueous Solution.

Authors:  Xiaowei Wu; Haitao Ji
Journal:  J Org Chem       Date:  2018-09-21       Impact factor: 4.354

2.  On the stereochemical course of palladium-catalyzed cross-coupling of allylic silanolate salts with aromatic bromides.

Authors:  Scott E Denmark; Nathan S Werner
Journal:  J Am Chem Soc       Date:  2010-03-17       Impact factor: 15.419

3.  Ruthenium(II)-Catalyzed Regio- and Stereoselective C-H Allylation of Indoles with Allyl Alcohols.

Authors:  Xiaowei Wu; Haitao Ji
Journal:  Org Lett       Date:  2018-03-27       Impact factor: 6.005
  3 in total

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