Literature DB >> 25678759

Regio- and Stereoselective Direct Cross-Coupling of Aromatic Imines with Allenic Alcohols.

Martin McLaughlin1, Heidi L Shimp1, Raul Navarro1, Glenn C Micalizio1.   

Abstract

We describe a titanium-mediated reaction for the convergent coupling of allenic alcohols with aromatic imines. Overall, the bond formation occurs at the central carbon of the allene, proceeds with net allylic transposition, and provides substituted 1,3-dienes bearing allylic amine functionality in a regio- and stereoselective fashion.

Entities:  

Keywords:  Imines; allenes; cross-coupling; metallacycles; titanium

Year:  2008        PMID： 25678759      PMCID： PMC4323354          DOI： 10.1055/s-2008-1042808

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  15 in total

1.  Allenes from cyclopropanes and their use in organic synthesis-recent developments.

Authors:  Leiv K Sydnes
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

2.  Vanadium-catalyzed anti-selective additions of allenols to imines.

Authors:  Barry M Trost; Catrin Jonasson
Journal:  Angew Chem Int Ed Engl       Date:  2003-05-09       Impact factor: 15.336

Review 3.  Chiral allylic and allenic metal reagents for organic synthesis.

Authors:  James A Marshall
Journal:  J Org Chem       Date:  2007-06-27       Impact factor: 4.354

4.  Aza-Baylis-Hillman reactions of N-tosylated aldimines with activated allenes and alkynes in the presence of various Lewis base promoters.

Authors:  Gui-Ling Zhao; Min Shi
Journal:  J Org Chem       Date:  2005-11-25       Impact factor: 4.354

5.  Allylpalladium umpolung in the three-component coupling synthesis of homoallylic amines.

Authors:  Chad D Hopkins; Helena C Malinakova
Journal:  Org Lett       Date:  2006-12-21       Impact factor: 6.005

6.  Synthesis of octahydroquinolines through the Lewis acid catalyzed reaction of vinyl allenes and imines.

Authors:  David Regás; María M Afonso; Matías L Rodríguez; J Antonio Palenzuela
Journal:  J Org Chem       Date:  2003-10-03       Impact factor: 4.354

7.  An expedient phosphine-catalyzed [4 + 2] annulation: synthesis of highly functionalized tetrahydropyridines.

Authors:  Xue-Feng Zhu; Jie Lan; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2003-04-23       Impact factor: 15.419

8.  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

9.  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

10.  Abnormal aza-Baylis-Hillman reaction of N-tosylated imines with ethyl 2,3-butadienoate and penta-3,4-dien-2-one.

Authors:  Gui-Ling Zhao; Jin-Wen Huang; Min Shi
Journal:  Org Lett       Date:  2003-11-27       Impact factor: 6.005
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  9 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.  Regioselective Reductive Cross-Coupling Reactions of Unsymmetrical Alkynes.

Authors:  Holly A Reichard; Martin McLaughlin; Ming Z Chen; Glenn C Micalizio
Journal:  European J Org Chem       Date:  2010-01

3.  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

4.  Convergent synthesis of stereodefined exo-alkylidene-gamma-lactams from beta-halo allylic alcohols.

Authors:  Shuhei Umemura; Martin McLaughlin; Glenn C Micalizio
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005

5.  Aliphatic imines in titanium-mediated reductive cross-coupling: unique reactivity of Ti(O-i-Pr)4/n-BuLi.

Authors:  Michael A Tarselli; Glenn C Micalizio
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

6.  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

7.  The regio- and stereochemical course of reductive cross-coupling reactions between 1,3-disubstituted allenes and vinylsilanes: Synthesis of (Z)-dienes.

Authors:  Allan U Barlan; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

8.  An annulation reaction for the synthesis of cross-conjugated triene-containing hydroindanes from acyclic precursors.

Authors:  Xiayun Cheng; Glenn C Micalizio
Journal:  Org Lett       Date:  2014-09-12       Impact factor: 6.005

9.  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
  9 in total

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