Literature DB >> 12487589

A rhodium(I)-catalyzed formal allenic Alder ene reaction for the rapid and stereoselective assembly of cross-conjugated trienes.

Kay M Brummond1, Hongfeng Chen, Peter Sill, Lingfeng You.   

Abstract

A rhodium(I)-catalyzed allenic Alder ene reaction to prepare cross-conjugated trienes has been discovered. The scope and limitations are currently being investigated, and the results obtained to date are reported on. This method shows enticing functional group compatibility by tolerating terminal and internal alkynes, hydroxyl, sulfonamide, ether, and diester groups. Progress has been made to increase the stereoselectivity of the olefinic side chain via an unprecendented iridium(I) catalyzed Alder-ene reaction.

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Year:  2002        PMID： 12487589     DOI： 10.1021/ja027588p

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


  9 in total

1.  Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction.

Authors:  Paul Ha-Yeon Cheong; Philip Morganelli; Michael R Luzung; K N Houk; F Dean Toste
Journal:  J Am Chem Soc       Date:  2008-03-08       Impact factor: 15.419

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.  Rhodium(I)-catalyzed allenic carbocyclization reaction affording delta- and epsilon-lactams.

Authors:  Kay M Brummond; Thomas O Painter; Donald A Probst; Branko Mitasev
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

4.  Skeletal and Appendage Diversity as Design Elements in the Synthesis of a Discovery Library of Nonaromatic Polycyclic 5-Iminooxazolidin-2-ones, Hydantoins, and Acylureas.

Authors:  S Werner; D M Turner; P G Chambers; K M Brummond
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

5.  Allene-alkyne cross-coupling for stereoselective synthesis of substituted 1,4-dienes and cross-conjugated trienes.

Authors:  Heidi L Shimp; Alissa Hare; Martin McLaughlin; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2008-04-14       Impact factor: 2.457

6.  Enantioselective synthesis of 5,7-bicyclic ring systems from axially chiral allenes using a Rh(I)-catalyzed cyclocarbonylation reaction.

Authors:  Francois Grillet; Kay M Brummond
Journal:  J Org Chem       Date:  2013-03-29       Impact factor: 4.354

7.  Synthesis of cross-conjugated trienes by rhodium-catalyzed dimerization of monosubstituted allenes.

Authors:  Tomoya Miura; Tsuneaki Biyajima; Takeharu Toyoshima; Masahiro Murakami
Journal:  Beilstein J Org Chem       Date:  2011-05-09       Impact factor: 2.883

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

9.  Efficient Heterogeneous Copper-Catalyzed Alder-Ene Reaction of Allenynamides to Pyrrolines.

Authors:  Zhiyao Zheng; Luca Deiana; Daniels Posevins; Abdolrahim A Rafi; Kaiheng Zhang; Magnus J Johansson; Cheuk-Wai Tai; Armando Córdova; Jan-E Bäckvall
Journal:  ACS Catal       Date:  2022-01-18       Impact factor: 13.084
  9 in total

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