Literature DB >> 12098254

Stereocontrolled synthesis of linear 22R-homoallylic sterols via a triflic acid-catalyzed 2-oxonia Cope rearrangement.

Teck-Peng Loh1, Qi-Ying Hu, Li-Ting Ma.   

Abstract

[reaction: see text] Poor stereoselectivity caused by the involvement of side reaction pathways was observed in the In(OTf)(3)-catalyzed allyl-transfer reaction (R = electron-withdrawing group). Subsequently, it was found that the employment of triflic acid (TFA) as catalyst could successfully suppress the side reaction pathways and, hence, achieve high stereoselectivity.

Entities:  

Year:  2002        PMID： 12098254     DOI： 10.1021/ol026136e

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


  4 in total

1.  Racemization in Prins cyclization reactions.

Authors:  Ramesh Jasti; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2006-10-18       Impact factor: 15.419

Review 2.  Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors:  Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-03       Impact factor: 15.336

3.  Solvolysis of a tetrahydropyranyl mesylate: mechanistic implications for the Prins cyclization, 2-oxonia-cope rearrangement, and Grob fragmentation.

Authors:  Ramesh Jasti; Scott D Rychnovsky
Journal:  Org Lett       Date:  2006-05-11       Impact factor: 6.005

4.  Enantio- and diastereoselective synthesis of syn-β-hydroxy-α-vinyl carboxylic esters via reductive aldol reactions of ethyl allenecarboxylate with 10-TMS-9-Borabicyclo[3.3.2]decane and DFT analysis of the hydroboration pathway.

Authors:  Jeremy Kister; Daniel H Ess; William R Roush
Journal:  Org Lett       Date:  2013-10-18       Impact factor: 6.005
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.