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Literature DB >> 19079735

Zirconium Bis(Amido) Catalysts for Asymmetric Intramolecular Alkene Hydroamination.

Donald A Watson¹, Melanie Chiu, Robert G Bergman.

Abstract

In situ combination of diphosphinic amides and Zr(NMe(2))(4) results in the formation of chiral zirconium bis(amido) complexes. The complexes are competent catalysts for intramolecular asymmetric alkene hydroamintion, providing piperidines and pyrrolidines in up to 80% ee and high yield. This system utilizes an inexpensive zirconium precatalyst and readily prepared ligands and is the first asymmetric alkene hydroamination catalyst based upon a neutral zirconium bis(amido) complex.

Entities: Chemical

Year: 2006 PMID： 19079735 PMCID： PMC2600731 DOI： 10.1021/om0606791

Source DB: PubMed Journal: Organometallics ISSN： 0276-7333 Impact factor: 3.876

17 in total

1. Palladium-catalyzed hydroamination of 1,3-dienes: a colorimetric assay and enantioselective additions.

Authors: O Löber; M Kawatsura; J F Hartwig
Journal: J Am Chem Soc Date: 2001-05-09 Impact factor: 15.419

2. Enantioselective catalytic hydroamination of alkenes.

Authors: Peter W Roesky; Thomas E Müller
Journal: Angew Chem Int Ed Engl Date: 2003-06-23 Impact factor: 15.336

3. Catalytic asymmetric hydroamination of non-activated olefins.

Authors: Kai C Hultzsch
Journal: Org Biomol Chem Date: 2005-04-07 Impact factor: 3.876

4. Lanthanide complexes coordinated by N-substituted (R)-1,1'-binaphthyl-2,2'-diamido ligands in the catalysis of enantioselective intramolecular hydroamination.

Authors: Jacqueline Collin; Jean-Claude Daran; Olivier Jacquet; Emmanuelle Schulz; Alexander Trifonov
Journal: Chemistry Date: 2005-05-20 Impact factor: 5.236

5. Palladium-catalyzed intramolecular asymmetric hydroamination, hydroalkoxylation, and hydrocarbonation of alkynes.

Authors: Nitin T Patil; Léopold Mpaka Lutete; Huanyou Wu; Nirmal K Pahadi; Ilya D Gridnev; Yoshinori Yamamoto
Journal: J Org Chem Date: 2006-05-26 Impact factor: 4.354

6. Base-catalysed asymmetric hydroamination/cyclisation of aminoalkenes utilising a dimeric chiral diamidobinaphthyl dilithium salt.

Authors: Patricia Horrillo Martínez; Kai C Hultzsch; Frank Hampel
Journal: Chem Commun (Camb) Date: 2006-04-11 Impact factor: 6.222

7. Intramolecular hydroamination of unactived olefins with Ti(NMe2)4 as a precatalyst.

Authors: Jason A Bexrud; J David Beard; David C Leitch; Laurel L Schafer
Journal: Org Lett Date: 2005-05-12 Impact factor: 6.005

8. Trifluoromethanesulfonamide, diphenylphosphoramide and diphenylthiophosphoramide of (R)-(+)-1,1'-binaphthyl-2,2'-diamine as chiral catalyst ligands for the titanium(IV) alkoxide-promoted addition of diethylzinc to aldehydes

Authors:
Journal: Chirality Date: 2000-07 Impact factor: 2.437

9. Use of group 4 bis(sulfonamido) complexes in the intramolecular hydroamination of alkynes and allenes.

Authors: Lutz Ackermann; Robert G Bergman; Rebecca N Loy
Journal: J Am Chem Soc Date: 2003-10-01 Impact factor: 15.419

10. Organolanthanide-catalyzed hydroamination.

Authors: Sukwon Hong; Tobin J Marks
Journal: Acc Chem Res Date: 2004-09 Impact factor: 22.384

8 in total

1. The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles.

Authors: Sherry R Chemler
Journal: Org Biomol Chem Date: 2009 Impact factor: 3.876

2. A stereocontrolled synthesis of (±)-xenovenine via a scandium(III)-catalyzed internal aminodiene bicyclization terminated by a 2-(5-ethyl-2-thienyl)ethenyl group.

Authors: Tao Jiang; Tom Livinghouse
Journal: Org Lett Date: 2010-10-01 Impact factor: 6.005

Zirconium Bis(Amido) Catalysts for Asymmetric Intramolecular Alkene Hydroamination.

1. Palladium-catalyzed hydroamination of 1,3-dienes: a colorimetric assay and enantioselective additions.

2. Enantioselective catalytic hydroamination of alkenes.

3. Catalytic asymmetric hydroamination of non-activated olefins.

4. Lanthanide complexes coordinated by N-substituted (R)-1,1'-binaphthyl-2,2'-diamido ligands in the catalysis of enantioselective intramolecular hydroamination.

5. Palladium-catalyzed intramolecular asymmetric hydroamination, hydroalkoxylation, and hydrocarbonation of alkynes.

6. Base-catalysed asymmetric hydroamination/cyclisation of aminoalkenes utilising a dimeric chiral diamidobinaphthyl dilithium salt.

7. Intramolecular hydroamination of unactived olefins with Ti(NMe2)4 as a precatalyst.

8. Trifluoromethanesulfonamide, diphenylphosphoramide and diphenylthiophosphoramide of (R)-(+)-1,1'-binaphthyl-2,2'-diamine as chiral catalyst ligands for the titanium(IV) alkoxide-promoted addition of diethylzinc to aldehydes

9. Use of group 4 bis(sulfonamido) complexes in the intramolecular hydroamination of alkynes and allenes.

10. Organolanthanide-catalyzed hydroamination.

1. The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles.

2. A stereocontrolled synthesis of (±)-xenovenine via a scandium(III)-catalyzed internal aminodiene bicyclization terminated by a 2-(5-ethyl-2-thienyl)ethenyl group.

3. 3-Aryl-2,5-Dihydropyrroles via Catalytic Carbonyl-Olefin Metathesis.

4. Rhodium-catalyzed asymmetric intramolecular hydroamination of unactivated alkenes.

5. Chiral Indoline Synthesis Via Enantioselective Intramolecular Copper-Catalyzed Alkene Hydroamination.

6. Enantioselective thiourea-catalyzed intramolecular cope-type hydroamination.

7. Anti-Markovnikov hydroamination of alkenes catalyzed by an organic photoredox system.

8. Bis(3,5-dimeth-oxy-phen-yl)phosphinic acid.