Literature DB >> 22128826

The Prins reaction using ketones: rationalization and application toward the synthesis of the portentol skeleton.

Maiwenn Jacolot1, Mickael Jean, Nicolas Levoin, Pierre van de Weghe.   

Abstract

We report a TMSI-promoted Prins cyclization reaction with ketones as carbonyl partners to prepare polysubstituted chiral spirotetrahydropyrans. In the presence of racemic 2-methylcyclohexanone a dynamic kinetic resolution occurred affording one stereoisomer. The observed enantiospecificity has been rationalized by DFT calculation.
© 2011 American Chemical Society

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Year:  2011        PMID： 22128826     DOI： 10.1021/ol202829u

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


  5 in total

Review 1.  Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.

Authors:  Imtiaz Khan; Aliya Ibrar; Sumera Zaib
Journal:  Top Curr Chem (Cham)       Date:  2021-01-05

2.  Mechanistic and computational studies of exocyclic stereocontrol in the synthesis of bryostatin-like cis-2,6-disubstituted 4-alkylidenetetrahydropyrans by Prins cyclization.

Authors:  Yasuyuki Ogawa; Phillip P Painter; Dean J Tantillo; Paul A Wender
Journal:  J Org Chem       Date:  2012-11-07       Impact factor: 4.354

3.  Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans.

Authors:  Hélio Faustino; Iván Varela; José L Mascareñas; Fernando López
Journal:  Chem Sci       Date:  2015-03-02       Impact factor: 9.825

4.  Iodine-catalyzed prins cyclization of homoallylic alcohols and aldehydes.

Authors:  Kachi R Kishore Kumar Reddy; Iara M L Rosa; Antônio C Doriguetto; Erick L Bastos; Luiz F Silva
Journal:  Molecules       Date:  2013-09-10       Impact factor: 4.411

5.  A new intermediate in the Prins reaction.

Authors:  Shinichi Yamabe; Takeshi Fukuda; Shoko Yamazaki
Journal:  Beilstein J Org Chem       Date:  2013-03-05       Impact factor: 2.883
  5 in total

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