Literature DB >> 24245533

Stereoselective and regioselective intramolecular Friedel-Crafts reaction of aziridinium ions for synthesis of 4-substituted tetrahydroisoquinolines.

Hyun-Soon Chong1, Yunwei Chen.   

Abstract

Optically active 4-substituted tetrahydroisoquinolines were synthesized via intramolecular Friedel-Crafts (FC) reactions of aziridinium ions in a highly regio- and stereoselective manner. Control experiments suggest the formation and ring-opening of aziridinium ions as the key intermediates in the Lewis acid catalyzed FC reactions.

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Year:  2013        PMID： 24245533      PMCID： PMC6423956          DOI： 10.1021/ol4013537

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


  15 in total

1.  Diamine synthesis: exploring the regioselectivity of ring opening of aziridinium ions.

Authors:  Peter O'Brien; Timothy D Towers
Journal:  J Org Chem       Date:  2002-01-11       Impact factor: 4.354

Review 2.  Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics.

Authors:  Jack D Scott; Robert M Williams
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

3.  Diastereoselective protonation of lactam enolates derived from (R)-phenylglycinol. A novel asymmetric route to 4-phenyl-1,2,3, 4-tetrahydroisoquinolines.

Authors:  N Philippe; V Levacher; G Dupas; G Quéguiner; J Bourguignon
Journal:  Org Lett       Date:  2000-07-27       Impact factor: 6.005

4.  Nucleophile-dependent regioselective ring opening of 2-substituted N,N-dibenzylaziridinium ions: bromide versus hydride.

Authors:  Sae Young Yun; Saron Catak; Won Koo Lee; Matthias D'hooghe; Norbert De Kimpe; Veronique Van Speybroeck; Michel Waroquier; Yongeun Kim; Hyun-Joon Ha
Journal:  Chem Commun (Camb)       Date:  2009-04-01       Impact factor: 6.222

5.  A new selective synthesis of the Ile-allo-Thr-Gly tripeptide fragment of lysobactin.

Authors:  S Armaroli; G Cardillo; L Gentilucci; M Gianotti; A Tolomelli
Journal:  Org Lett       Date:  2000-04-20       Impact factor: 6.005

6.  Ring-Opening Cycloaddition of Aziridines to Ketenimines.

Authors:  Heiko Maas; Corinne Bensimon; Howard Alper
Journal:  J Org Chem       Date:  1998-01-09       Impact factor: 4.354

7.  A Theoretical and Experimental Study on Acid-Catalyzed Isomerization of 1-Acylaziridines to the Oxazolines. Reexamination of a Possible S(N)i Mechanism by Using ab Initio Molecular Orbital Calculations.

Authors:  Kenzi Hori; Takeshi Nishiguchi; Aiko Nabeya
Journal:  J Org Chem       Date:  1997-05-16       Impact factor: 4.354

8.  Chiral anion-mediated asymmetric ring opening of meso-aziridinium and episulfonium ions.

Authors:  Gregory L Hamilton; Toshio Kanai; F Dean Toste
Journal:  J Am Chem Soc       Date:  2008-10-21       Impact factor: 15.419

9.  Total synthesis of (+/-)-haouamine A.

Authors:  Phil S Baran; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2006-03-29       Impact factor: 15.419

Review 10.  Dopamine D1 receptor ligands: where are we now and where are we going.

Authors:  Jing Zhang; Bing Xiong; Xuechu Zhen; Ao Zhang
Journal:  Med Res Rev       Date:  2009-03       Impact factor: 12.944
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  1 in total

1.  Application of aziridinium ring opening for preparation of optically active diamine and triamine analogues: Highly efficient synthesis and evaluation of DTPA-based MRI contrast enhancement agents.

Authors:  Xiang Sun; Yunwei Chen; Ningjie Wu; Chi Soo Kang; Hyun A Song; Shengnan Jin; Yao Fu; Henry Bryant; Joseph A Frank; Hyun-Soon Chong
Journal:  RSC Adv       Date:  2015-11-03       Impact factor: 3.361
  1 in total

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