Literature DB >> 12375919

Intramolecular Baylis-Hillman and morita reactions using unsaturated thiol ester substrates containing enolizable aldehydes.

Gary E Keck1, Dennie S Welch.   

Abstract

[reaction: see text] Previously unknown intramolecular Baylis-Hillman and Morita reactions involving cyclization of an unsaturated thiol ester onto a pendant aldehyde function are reported. These can be used successfully for the preparation of both cyclopentenols and cyclohexenols, but the results are very sensitive to substrate and precise reaction conditions.

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Year:  2002        PMID： 12375919      PMCID： PMC1480409          DOI： 10.1021/ol026638s

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


  4 in total

1.  Rate acceleration of the Baylis-Hillman reaction in polar solvents (water and formamide). Dominant role of hydrogen bonding, not hydrophobic effects, is implicated.

Authors:  Varinder K Aggarwal; David K Dean; Andrea Mereu; Richard Williams
Journal:  J Org Chem       Date:  2002-01-25       Impact factor: 4.354

2.  Efficient Baylis--Hillman reaction using stoichiometric base catalyst and an aqueous medium.

Authors:  C Yu; B Liu; L Hu
Journal:  J Org Chem       Date:  2001-08-10       Impact factor: 4.354

3.  Organocatalytic Michael cycloisomerization of bis(enones): the intramolecular Rauhut-Currier reaction.

Authors:  Long-Cheng Wang; Ana Liza Luis; Kyriacos Agapiou; Hye-Young Jang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

4.  The vinylogous intramolecular Morita-Baylis-Hillman reaction: synthesis of functionalized cyclopentenes and cyclohexenes with trialkylphosphines as nucleophilic catalysts.

Authors:  Scott A Frank; Dustin J Mergott; William R Roush
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419
  4 in total
  4 in total

1.  Enantioselective hydrogenation of alpha-aminomethylacrylates containing a free NH group for the synthesis of beta-amino acid derivatives.

Authors:  Liqin Qiu; Mahavir Prashad; Bin Hu; Kapa Prasad; Oljan Repic; Thomas J Blacklock; Fuk Yee Kwong; Stanton H L Kok; Hang Wai Lee; Albert S C Chan
Journal:  Proc Natl Acad Sci U S A       Date:  2007-10-17       Impact factor: 11.205

2.  Synthesis of sultam scaffolds via intramolecular oxa-Michael and diastereoselective Baylis-Hillman reactions.

Authors:  Aihua Zhou; Paul R Hanson
Journal:  Org Lett       Date:  2008-06-14       Impact factor: 6.005

Review 3.  Enantioselective, organocatalytic Morita-Baylis-Hillman and Aza-Morita-Baylis-Hillman reactions: stereochemical issues.

Authors:  Javier Mansilla; José M Saá
Journal:  Molecules       Date:  2010-02-01       Impact factor: 4.411

4.  Design, Synthesis, and Study of a Novel RXPA380-Proline Hybrid (RXPA380-P) as an Antihypertensive Agent.

Authors:  Moaz M Abdou; Dewen Dong; Paul M O'Neill; Eric Amigues; Magdalini Matziari
Journal:  ACS Omega       Date:  2022-09-23
  4 in total

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