Literature DB >> 19275160

Asymmetric synthesis of diamine derivatives via sequential palladium and rhodium catalysis.

Barry M Trost1, Sushant Malhotra, David E Olson, Autumn Maruniak, J Du Bois.   

Abstract

The use of a bifunctional nitrogen nucleophile and an allyl carbonate starting material in successive enantioselective palladium- and diastereoselective rhodium-catalyzed reactions enables the rapid assembly of unique amino aziridine products. Further elaboration of these materials affords complex, stereodefined polyamine architectures, thus demonstrating the power of these combined methods for simplifying asymmetric C-N bond construction.

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Year:  2009        PMID： 19275160      PMCID： PMC3235049          DOI： 10.1021/ja809697p

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  10 in total

1.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors:  Barry M Trost; Matthew L Crawley
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

Review 2.  2-Deoxystreptamine: central scaffold of aminoglycoside antibiotics.

Authors:  Guuske F Busscher; Floris P J T Rutjes; Floris L van Delft
Journal:  Chem Rev       Date:  2005-03       Impact factor: 60.622

3.  Chiral tertiary diamines in asymmetric synthesis.

Authors:  Jean-Claude Kizirian
Journal:  Chem Rev       Date:  2007-12-15       Impact factor: 60.622

4.  Transition-metal-catalyzed diamination of olefins.

Authors:  Renata Marcia de Figueiredo
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  Enantioselective organocatalytic direct Michael addition of nitroalkanes to nitroalkenes promoted by a unique bifunctional DMAP-thiourea.

Authors:  Constantinos Rabalakos; William D Wulff
Journal:  J Am Chem Soc       Date:  2008-09-23       Impact factor: 15.419

6.  Palladium-catalyzed DYKAT of butadiene monoepoxide: enantioselective total synthesis of (+)-DMDP, (-)-bulgecinine, and (+)-broussonetine G.

Authors:  Barry M Trost; Daniel B Horne; Michael J Woltering
Journal:  Chemistry       Date:  2006-08-25       Impact factor: 5.236

7.  Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: a working model.

Authors:  Barry M Trost; Michelle R Machacek; Aaron Aponick
Journal:  Acc Chem Res       Date:  2006-10       Impact factor: 22.384

8.  Catalytic C-H amination for the preparation of substituted 1,2-diamines.

Authors:  David E Olson; J Du Bois
Journal:  J Am Chem Soc       Date:  2008-08-05       Impact factor: 15.419

Review 9.  Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry.

Authors:  S R S Saibabu Kotti; Cody Timmons; Guigen Li
Journal:  Chem Biol Drug Des       Date:  2006-02       Impact factor: 2.817

10.  A general one-step synthesis of beta-nitronitriles.

Authors:  James C Anderson; Alexander J Blake; Matthew Mills; Paul D Ratcliffe
Journal:  Org Lett       Date:  2008-08-23       Impact factor: 6.005
  10 in total
  9 in total

1.  1,4-Diazaspiro[2.2]pentanes as a flexible platform for the synthesis of diamine-bearing stereotriads.

Authors:  Jared W Rigoli; Luke A Boralsky; John C Hershberger; Dagmara Marston; Alan R Meis; Ilia A Guzei; Jennifer M Schomaker
Journal:  J Org Chem       Date:  2012-02-14       Impact factor: 4.354

2.  Nickel-Catalyzed Allylic Alkylation with Diarylmethane Pronucleophiles: Reaction Development and Mechanistic Insights.

Authors:  Sheng-Chun Sha; Hui Jiang; Jianyou Mao; Ana Bellomo; Soo A Jeong; Patrick J Walsh
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-03       Impact factor: 15.336

3.  Computationally guided stereocontrol of the combined C-H functionalization/Cope rearrangement.

Authors:  Yajing Lian; Kenneth I Hardcastle; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-30       Impact factor: 15.336

4.  Synthesis and reactivity of unique heterocyclic structures en route to substituted diamines.

Authors:  David E Olson; Autumn Maruniak; Sushant Malhotra; Barry M Trost; J Du Bois
Journal:  Org Lett       Date:  2011-05-27       Impact factor: 6.005

5.  Modular synthesis of 1,2-diamine derivatives by palladium-catalyzed aerobic oxidative cyclization of allylic sulfamides.

Authors:  Richard I McDonald; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2010-07-26       Impact factor: 15.336

6.  Modular Synthesis of 1,2-Diamine Derivatives via Palladium-Catalyzed Aerobic Oxidative Cyclization of Allylic Sulfamides.

Authors:  Richard I McDonald; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2010-07-26       Impact factor: 15.336

7.  Effective synthesis of bicyclodienes via palladium-catalyzed asymmetric allylic alkylation and ruthenium-catalyzed cycloisomerization.

Authors:  Nizam Havare
Journal:  Turk J Chem       Date:  2020-12-16       Impact factor: 1.239

8.  Dinuclear PhosphoiminoBINOL-Pd Container for Malononitrile: Catalytic Asymmetric Double Mannich Reaction for Chiral 1,3-Diamine Synthesis.

Authors:  Takayoshi Arai; Katsuya Sato; Ayu Nakamura; Hiroki Makino; Hyuma Masu
Journal:  Sci Rep       Date:  2018-01-16       Impact factor: 4.379

9.  Ritter-enabled catalytic asymmetric chloroamidation of olefins.

Authors:  Daniel C Steigerwald; Bardia Soltanzadeh; Aritra Sarkar; Cecilia C Morgenstern; Richard J Staples; Babak Borhan
Journal:  Chem Sci       Date:  2020-12-07       Impact factor: 9.825
  9 in total

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