Literature DB >> 34290458

Rhodium(III)-Catalyzed Three-Component 1,2-Diamination of Unactivated Terminal Alkenes.

Sumin Lee1, Young Jin Jang1, Erik J T Phipps1, Honghui Lei1, Tomislav Rovis1.   

Abstract

We report a three-component diamination of simple unactivated alkenes using an electrophilic nitrene source and amine nucleophiles. The reaction provides rapid access to 1,2-vicinal diamines from terminal alkenes through a one-pot protocol. The transformation proceeds smoothly with excellent tolerance for a broad array of primary and secondary amines, affording the desired product with good yield and regioselectivity. The mechanism is proposed to proceed through a Rh(III)-catalyzed aziridination of alkenes with subsequent ring opening by primary or secondary amines.

Entities:  

Keywords:  One-pot synthesis; Rh(III)-catalysis; alkene diamination; nitrene

Year:  2020        PMID: 34290458      PMCID: PMC8290961          DOI: 10.1055/s-0039-1690756

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN: 0039-7881            Impact factor:   3.157


  19 in total

1.  A facile Pd(0)-catalyzed regio- and stereoselective diamination of conjugated dienes and trienes.

Authors:  Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

2.  Copper-Catalyzed Oxyboration of Unactivated Alkenes.

Authors:  Taisuke Itoh; Takumi Matsueda; Yohei Shimizu; Motomu Kanai
Journal:  Chemistry       Date:  2015-09-17       Impact factor: 5.236

3.  Cyclopropenimine-catalyzed enantioselective Mannich reactions of tert-butyl glycinates with N-Boc-imines.

Authors:  Jeffrey S Bandar; Tristan H Lambert
Journal:  J Am Chem Soc       Date:  2013-08-01       Impact factor: 15.419

4.  Metal-catalyzed electrochemical diazidation of alkenes.

Authors:  Niankai Fu; Gregory S Sauer; Ambarneil Saha; Aaron Loo; Song Lin
Journal:  Science       Date:  2017-08-11       Impact factor: 47.728

5.  Pd(II)-catalyzed intermolecular 1,2-diamination of conjugated dienes.

Authors:  Grégory L J Bar; Guy C Lloyd-Jones; Kevin I Booker-Milburn
Journal:  J Am Chem Soc       Date:  2005-05-25       Impact factor: 15.419

6.  An asymmetric nitro-Mannich reaction applicable to alkyl, aryl, and heterocyclic imines.

Authors:  James C Anderson; Gareth P Howell; Ron M Lawrence; Claire S Wilson
Journal:  J Org Chem       Date:  2005-07-08       Impact factor: 4.354

7.  Palladium(II)-catalyzed intramolecular diamination of unfunctionalized alkenes.

Authors:  Jan Streuff; Claas H Hövelmann; Martin Nieger; Kilian Muñiz
Journal:  J Am Chem Soc       Date:  2005-10-26       Impact factor: 15.419

Review 8.  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

9.  A Rh(III)-Catalyzed Formal [4+1] Approach to Pyrrolidines from Unactivated Terminal Alkenes and Nitrene Sources.

Authors:  Sumin Lee; Honghui Lei; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2019-08-05       Impact factor: 15.419

Review 10.  The Chemistry of Vicinal Diamines.

Authors:  Denis Lucet; Thierry Le Gall; Charles Mioskowski
Journal:  Angew Chem Int Ed Engl       Date:  1998-10-16       Impact factor: 15.336

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  3 in total

1.  Rh(III)-Catalyzed Three-Component Syn-Carboamination of Alkenes Using Arylboronic Acids and Dioxazolones.

Authors:  Sumin Lee; Tomislav Rovis
Journal:  ACS Catal       Date:  2021-06-30       Impact factor: 13.700

2.  N-Alkylation/aldol reaction of α-aldimino thioesters: a facile three-component coupling reaction.

Authors:  Makoto Shimizu; Asako Higashino; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2021-04-07       Impact factor: 3.361

Review 3.  The advent of electrophilic hydroxylamine-derived reagents for the direct preparation of unprotected amines.

Authors:  Valentina C M Gasser; Szabolcs Makai; Bill Morandi
Journal:  Chem Commun (Camb)       Date:  2022-09-08       Impact factor: 6.065

  3 in total

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