Literature DB >> 15070317

An unusual approach to the synthesis of enantiomerically cis linear homoallylic alcohols based on the steric interaction mechanism of camphor scaffold.

Chi-Lik Ken Lee1, Cheng-Hsia Angeline Lee, Kui-Thong Tan, Teck-Peng Loh.   

Abstract

Camphor is used as the chiral auxiliary for the enantioselective synthesis of cis linear homoallylic alcohols. A range of catalysts, aldehydes, and solvents were investigated to obtain the optimum yield, enantioselectivity, and cis olefinic geometry. [structure: see text]

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Year:  2004        PMID： 15070317     DOI： 10.1021/ol049633z

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


  10 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

2.  A highly enantio- and diastereoselective 1,3-dimethylallylation of aldehydes.

Authors:  Yu Yuan; Amy J Lai; Christina M Kraml; Chulbom Lee
Journal:  Tetrahedron       Date:  2006-12-04       Impact factor: 2.457

3.  Highly (E)-selective BF(3).Et(2)O-promoted allylboration of chiral nonracemic alpha-substituted allylboronates and analysis of the origin of stereocontrol.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

4.  A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing a Z-Alkenyl Chloride or Trifluoromethyl Group. A Concise and Protecting Group-Free Synthesis of Mycothiazole.

Authors:  Ryan J Morrison; Farid W van der Mei; Filippo Romiti; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2019-12-24       Impact factor: 15.419

5.  Stereoselective synthesis of tertiary ethers through geometric control of highly substituted oxocarbenium ions.

Authors:  Lei Liu; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-09       Impact factor: 15.336

Review 6.  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

7.  New chiral synthons for efficient introduction of bispropionates via stereospecific oxonia-cope rearrangements.

Authors:  Yi-Hung Chen; Frank E McDonald
Journal:  J Am Chem Soc       Date:  2006-04-12       Impact factor: 15.419

8.  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

9.  Correlation analysis of the rates of solvolysis of 4-bromopiperidine: a reaction following a Grob fragmentation pathway.

Authors:  Dennis Neil Kevill; Zoon Ha Ryu; Malcolm John D'Souza
Journal:  Eur J Chem       Date:  2017-06-30

Review 10.  Contemporary Strategies for the Synthesis of Tetrahydropyran Derivatives: Application to Total Synthesis of Neopeltolide, a Marine Macrolide Natural Product.

Authors:  Haruhiko Fuwa
Journal:  Mar Drugs       Date:  2016-03-25       Impact factor: 5.118
  10 in total

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