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Literature DB >> 19360820

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

Masayuki Takahashi¹, Martin McLaughlin, Glenn C Micalizio.

Abstract

Regioselective, stereoselective: The convergent coupling of allylic alcohols with imines to deliver stereodefined homoallylic amines is described (see scheme). The process proceeds with net allylic transposition without the intermediacy of allylic organometallic reagents. Two stereodefined centers and a geometrically defined di- or trisubstituted alkene are forged with high selectivity.

Entities: Chemical Gene

Mesh：

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Year: 2009 PMID： 19360820 PMCID： PMC3028933 DOI： 10.1002/anie.200900236

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

25 in total

1. Allylsilane-vinylarene cross-metathesis enables a powerful approach to enantioselective imine allylation.

Authors: John D Huber; Nicholas R Perl; James L Leighton
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

2. Synthesis of homoallylic amines by hydrozirconation-imine addition of allenes.

Authors: Peter Wipf; Joshua G Pierce
Journal: Org Lett Date: 2005-08-04 Impact factor: 6.005

3. Palladium-catalyzed allylation of imines with allyl alcohols.

Authors: Masamichi Shimizu; Masanari Kimura; Toshiya Watanabe; Yoshinao Tamaru
Journal: Org Lett Date: 2005-02-17 Impact factor: 6.005

4. Asymmetric allylboration of cyclic imines and applications to alkaloid synthesis.

Authors: T Robert Wu; J Michael Chong
Journal: J Am Chem Soc Date: 2006-08-02 Impact factor: 15.419

5. 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

6. Petasis Borono-Mannich reaction and allylation of carbonyl compounds via transient allyl boronates generated by palladium-catalyzed substitution of allyl alcohols. an efficient one-pot route to stereodefined alpha-amino acids and homoallyl alcohols.

Authors: Nicklas Selander; Andreas Kipke; Sara Sebelius; Kalman J Szabó
Journal: J Am Chem Soc Date: 2007-10-12 Impact factor: 15.419

7. Asymmetric allylboration of acyl imines catalyzed by chiral diols.

Authors: Sha Lou; Philip N Moquist; Scott E Schaus
Journal: J Am Chem Soc Date: 2007-11-17 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. Chiral bis-pi-allylpalladium complex catalyzed asymmetric allylation of imines: enhancement of the enantioselectivity and chemical yield in the presence of water.

Authors: Rodney A Fernandes; Anton Stimac; Yoshinori Yamamoto
Journal: J Am Chem Soc Date: 2003-11-19 Impact factor: 15.419

10. Toward a versatile allylation reagent: practical, enantioselective allylation of acylhydrazones using strained silacycles.

Authors: Richard Berger; Philippe M A Rabbat; James L Leighton
Journal: J Am Chem Soc Date: 2003-08-13 Impact factor: 15.419

18 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. 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

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. 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

5. 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

6. Convergent and stereodivergent synthesis of complex 1-aza-7-oxabicyclo[2.2.1]heptanes.

Authors: Dexi Yang; Glenn C Micalizio
Journal: J Am Chem Soc Date: 2011-05-23 Impact factor: 15.419

7. Catalytic Z-selective cross-metathesis with secondary silyl- and benzyl-protected allylic ethers: mechanistic aspects and applications to natural product synthesis.

Authors: Tyler J Mann; Alexander W H Speed; Richard R Schrock; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2013-06-21 Impact factor: 15.336

8. Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective γ-Additions of Allylboron Moieties to Aldimines.

Authors: Farid W van der Mei; Hiroshi Miyamoto; Daniel L Silverio; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2016-03-09 Impact factor: 15.336

9. 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

10. 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