Literature DB >> 15200310

Rhodium(I)-catalyzed ene-allene carbocyclization strategy for the formation of azepines and oxepines.

Kay M Brummond1, Hongfeng Chen, Branko Mitasev, Anthony D Casarez.   

Abstract

[reaction: see text] A novel strategy for the preparation of seven-membered heterocyclic compounds has been realized. Treatment of ene-allene 1 with a catalytic quantity of rhodium biscarbonyl chloride dimer affords the cyclization product 2 in moderate to high yields. The scope and limitations of this new method are currently under investigation, and the results obtained to date are discussed within.

Entities:  

Year:  2004        PMID： 15200310     DOI： 10.1021/ol049390a

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


  8 in total

1.  Toward the Ideal Synthesis and Transformative Therapies: The Roles of Step Economy and Function Oriented Synthesis.

Authors:  Paul A Wender
Journal:  Tetrahedron       Date:  2013-06-07       Impact factor: 2.457

2.  Computational Insight Concerning Catalytic Decision Points of the Transition Metal Catalyzed [2 + 2 + 1] Cyclocarbonylation Reaction of Allenes.

Authors:  Alexander S Bayden; Kay M Brummond; Kenneth D Jordan
Journal:  Organometallics       Date:  2006-10-23       Impact factor: 3.876

3.  Chemical methodology as a source of small-molecule checkpoint inhibitors and heat shock protein 70 (Hsp70) modulators.

Authors:  Donna M Huryn; Jeffrey L Brodsky; Kay M Brummond; Peter G Chambers; Benjamin Eyer; Alex W Ireland; Masaoki Kawasumi; Matthew G Laporte; Kayla Lloyd; Baptiste Manteau; Paul Nghiem; Bettina Quade; Sandlin P Seguin; Peter Wipf
Journal:  Proc Natl Acad Sci U S A       Date:  2011-04-18       Impact factor: 11.205

4.  Solution-phase synthesis of a tricyclic pyrrole-2-carboxamide discovery library applying a stetter-Paal-Knorr reaction sequence.

Authors:  Stefan Werner; Pravin S Iyer; Matthew D Fodor; Claire M Coleman; Leslie A Twining; Branko Mitasev; Kay M Brummond
Journal:  J Comb Chem       Date:  2006 May-Jun

5.  Design and synthesis of a library of tetracyclic hydroazulenoisoindoles.

Authors:  Kay M Brummond; Shuli Mao; Sunita N Shinde; Paul J Johnston; Billy W Day
Journal:  J Comb Chem       Date:  2009 May-Jun

6.  Reactivity and chemoselectivity of allenes in Rh(I)-catalyzed intermolecular (5 + 2) cycloadditions with vinylcyclopropanes: allene-mediated rhodacycle formation can poison Rh(I)-catalyzed cycloadditions.

Authors:  Xin Hong; Matthew C Stevens; Peng Liu; Paul A Wender; K N Houk
Journal:  J Am Chem Soc       Date:  2014-11-24       Impact factor: 15.419

7.  A thiocyanopalladation/carbocyclization transformation identified through enzymatic screening: stereocontrolled tandem C-SCN and C-C bond formation.

Authors:  G Malik; R A Swyka; V K Tiwari; X Fei; G A Applegate; D B Berkowitz
Journal:  Chem Sci       Date:  2017-10-03       Impact factor: 9.825

8.  A rhodium catalyzed cycloisomerization and tandem Diels-Alder reaction for facile access to diverse bicyclic and tricyclic heterocycles.

Authors:  Yirong Zhou; Ali Nikbakht; Felix Bauer; Bernhard Breit
Journal:  Chem Sci       Date:  2019-04-03       Impact factor: 9.825
  8 in total

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