Literature DB >> 18985173

Allene-alkyne cross-coupling for stereoselective synthesis of substituted 1,4-dienes and cross-conjugated trienes.

Heidi L Shimp1, Alissa Hare, Martin McLaughlin, Glenn C Micalizio.   

Abstract

Titanium-mediated cross-coupling of allenic alcohols with alkynes has been investigated. Divergent reaction pathways were discovered that provide either stereodefined 1,4-dienes or substituted cross-conjugated trienes. In short, allene substitution plays a critical role in the determination of reaction pathway.

Entities:  

Year:  2008        PMID： 18985173      PMCID： PMC2577592          DOI： 10.1016/j.tet.2008.02.015

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  14 in total

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Authors:  B M Trost; F D Toste; A B Pinkerton
Journal:  Chem Rev       Date:  2001-07       Impact factor: 60.622

2.  Tandem Dielsminus signAlder Cycloadditions in Organic Synthesis.

Authors:  Jeffrey D. Winkler
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

3.  A site- and stereoselective intermolecular alkene-alkyne coupling process.

Authors:  Holly A Reichard; Glenn C Micalizio
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Regio- and stereoselective cross-coupling of substituted olefins and imines. A convergent stereoselective synthesis of saturated 1,5-amino-alcohols and substituted piperidines.

Authors:  Masayuki Takahashi; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2007-05-26       Impact factor: 15.419

5.  Palladium-catalyzed cross-coupling reactions in total synthesis.

Authors:  K C Nicolaou; Paul G Bulger; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-18       Impact factor: 15.336

6.  An alkoxide-directed carbometalation of internal alkynes.

Authors:  Jamie Ryan; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

Review 7.  Nickel-catalyzed reductive cyclizations and couplings.

Authors:  John Montgomery
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-26       Impact factor: 15.336

8.  Cross-coupling for cross-conjugation: practical synthesis and Diels-Alder reactions of [3]dendralenes.

Authors:  Tanya A Bradford; Alan D Payne; Anthony C Willis; Michael N Paddon-Row; Michael S Sherburn
Journal:  Org Lett       Date:  2007-10-11       Impact factor: 6.005

9.  An alkoxide-directed alkyne-allene cross-coupling for stereoselective synthesis of 1,4-dienes.

Authors:  Heidi L Shimp; Glenn C Micalizio
Journal:  Chem Commun (Camb)       Date:  2007-08-23       Impact factor: 6.222

10.  An alkoxide-directed intermolecular [2+2+1] annulation: a three-component coupling reaction for the synthesis of tetrasubstituted alpha,beta-unsaturated gamma-lactams.

Authors:  Martin McLaughlin; Masayuki Takahashi; Glenn C Micalizio
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336
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  5 in total

1.  Reaction design, discovery, and development as a foundation to function-oriented synthesis.

Authors:  Glenn C Micalizio; Sarah B Hale
Journal:  Acc Chem Res       Date:  2015-02-10       Impact factor: 22.384

2.  Conversion of allylic alcohols to stereodefined trisubstituted alkenes: a complementary process to the Claisen rearrangement.

Authors:  Justin K Belardi; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2008-12-17       Impact factor: 15.419

3.  Complex allylation by the direct cross-coupling of imines with unactivated allylic alcohols.

Authors:  Masayuki Takahashi; Martin McLaughlin; Glenn C Micalizio
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Synthesis of cross-conjugated trienes by rhodium-catalyzed dimerization of monosubstituted allenes.

Authors:  Tomoya Miura; Tsuneaki Biyajima; Takeharu Toyoshima; Masahiro Murakami
Journal:  Beilstein J Org Chem       Date:  2011-05-09       Impact factor: 2.883

5.  Azaphilic versus Carbophilic Coupling at C=N Bonds: Key Steps in Titanium-Assisted Multicomponent Reactions.

Authors:  Torsten Roth; Hubert Wadepohl; Eric Clot; Lutz H Gade
Journal:  Chemistry       Date:  2015-11-06       Impact factor: 5.236
  5 in total

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