Literature DB >> 19810765

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

Michael A Tarselli1, Glenn C Micalizio.   

Abstract

A procedure for the coupling of aliphatic imines with allylic and allenic alkoxides is described. The success of these studies was enabled by a unique reactivity profile of Ti(IV) isopropoxide/n-BuLi compared to well-known Ti(IV) isopropoxide/RMgX systems.

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Year:  2009        PMID： 19810765      PMCID： PMC2818175          DOI： 10.1021/ol901870n

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


  13 in total

1.  Catalytic enantioselective addition to imines.

Authors:  S Kobayashi; H Ishitani
Journal:  Chem Rev       Date:  1999-05-12       Impact factor: 60.622

2.  Catalytic three-component coupling of alkynes, imines, and organoboron reagents.

Authors:  Sejal J Patel; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2003-03-28       Impact factor: 15.336

3.  Allylic amines via iridium-catalyzed C-C bond forming hydrogenation: imine vinylation in the absence of stoichiometric byproducts or metallic reagents.

Authors:  Andriy Barchuk; Ming-Yu Ngai; Michael J Krische
Journal:  J Am Chem Soc       Date:  2007-06-16       Impact factor: 15.419

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.  Hydrogen-mediated reductive coupling of conjugated alkynes with ethyl (N-Sulfinyl)iminoacetates: synthesis of unnatural alpha-amino acids via rhodium-catalyzed C-C bond forming hydrogenation.

Authors:  Jong-Rock Kong; Chang-Woo Cho; Michael J Krische
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

6.  Enantioselective reductive coupling of acetylene to N-arylsulfonyl imines via rhodium catalyzed C-C bond-forming hydrogenation: (Z)-dienyl allylic amines.

Authors:  Eduardas Skucas; Jong Rock Kong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2007-05-19       Impact factor: 15.419

7.  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

8.  Recent Applications of Imines as Key Intermediates in the Synthesis of Alkaloids and Novel Nitrogen Heterocycles.

Authors:  Stephen F Martin
Journal:  Pure Appl Chem       Date:  2009       Impact factor: 2.453

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.  Stereoselective cross-coupling between allylic alcohols and aldimines.

Authors:  Ivan L Lysenko; Hyung Goo Lee; Jin Kun Cha
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005
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  16 in total

1.  Preparation of stereodefined homoallylic amines from the reductive cross-coupling of allylic alcohols with imines.

Authors:  Ming Z Chen; Martin McLaughlin; Masayuki Takahashi; Michael A Tarselli; Dexi Yang; Shuhei Umemura; Glenn C Micalizio
Journal:  J Org Chem       Date:  2010-11-11       Impact factor: 4.354

2.  Synthesis of Highly Functionalized Decalins via Metallacycle-Mediated Cross-Coupling.

Authors:  Haruki Mizoguchi; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2015-05-12       Impact factor: 15.419

3.  Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.

Authors:  Natasha F O'Rourke; Matthew J Kier; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2016-09-07       Impact factor: 2.457

4.  Generation of quaternary centers by reductive cross-coupling: shifting of regioselectivity in a subset of allylic alcohol-based coupling reactions.

Authors:  Dexi Yang; Justin K Belardi; Glenn C Micalizio
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

5.  Cyclopropenes in Metallacycle-Mediated Cross-Coupling with Alkynes: Convergent Synthesis of Highly Substituted Vinylcyclopropanes.

Authors:  Natasha F O'Rourke; Glenn C Micalizio
Journal:  Org Lett       Date:  2016-03-01       Impact factor: 6.005

6.  In Situ Catalyst Generation and Benchtop-Compatible Entry Points for TiII/TiIV Redox Catalytic Reactions.

Authors:  Zachary W Davis-Gilbert; Kento Kawakita; Daniel R Blechschmidt; Hayato Tsurugi; Kazushi Mashima; Ian A Tonks
Journal:  Organometallics       Date:  2018-09-06       Impact factor: 3.876

7.  A convergent stereoselective synthesis of quinolizidines and indolizidines: chemoselective coupling of 2-hydroxymethyl-substituted allylic silanes with imines.

Authors:  Dexi Yang; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2009-12-09       Impact factor: 15.419

8.  Stereochemical lability of azatitanacyclopropanes: dynamic kinetic resolution in reductive cross-coupling reactions with allylic alcohols.

Authors:  Dexi Yang; Glenn C Micalizio
Journal:  Chem Commun (Camb)       Date:  2013-10-09       Impact factor: 6.222

9.  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

10.  Generation of Masked TiII Intermediates from TiIV Amides via β-H Abstraction or Alkyne Deprotonation: An Example of Ti-Catalyzed Nitrene-Coupled Transfer Hydrogenation.

Authors:  Adam J Pearce; Yukun Cheng; Rachel J Dunscomb; Ian A Tonks
Journal:  Organometallics       Date:  2020-10-20       Impact factor: 3.876
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