Literature DB >> 19711950

Enantioselective rhodium-catalyzed [4+2+2] cycloaddition of dienyl isocyanates for the synthesis of bicyclic azocine rings.

Robert T Yu1, Rebecca Keller Friedman, Tomislav Rovis.   

Abstract

A highly enantioselective rhodium-catalyzed [4+2+2] cycloaddition of terminal alkynes and dienyl isocyanates has been developed. The cycloaddition provides a rapid entry to highly functionalized and enantioenriched bicyclic azocines. This reaction represents the first [4+2+2] cycloaddition strategy to construct nitrogen-containing eight-membered rings.

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Year:  2009        PMID： 19711950      PMCID： PMC2774260          DOI： 10.1021/ja906641d

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


  27 in total

1.  Diastereoselective metal-catalyzed [4 + 2 + 2] carbocyclization reactions utilizing a rhodium N-heterocyclic carbene (NHC) complex: the first example of a rhodium NHC-catalyzed [m + n + o] carbocyclization.

Authors:  P Andrew Evans; Erich W Baum; Aleem N Fazal; Maren Pink
Journal:  Chem Commun (Camb)       Date:  2004-11-19       Impact factor: 6.222

2.  Design, synthesis, and characterization of a potent, nonpeptide, cell-permeable, bivalent Smac mimetic that concurrently targets both the BIR2 and BIR3 domains in XIAP.

Authors:  Haiying Sun; Zaneta Nikolovska-Coleska; Jianfeng Lu; Jennifer L Meagher; Chao-Yie Yang; Su Qiu; York Tomita; Yumi Ueda; Sheng Jiang; Krzysztof Krajewski; Peter P Roller; Jeanne A Stuckey; Shaomeng Wang
Journal:  J Am Chem Soc       Date:  2007-11-14       Impact factor: 15.419

3.  Synthesis of 5/7-, 5/8- and 5/9-bicyclic lactam templates as constraints for external beta-turns.

Authors:  Heather M E Duggan; Peter B Hitchcock; Douglas W Young
Journal:  Org Biomol Chem       Date:  2005-05-10       Impact factor: 3.876

4.  Rhodium-catalyzed [2 + 2 + 2] cycloaddition of alkenyl isocyanates and alkynes.

Authors:  Robert T Yu; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

5.  Enantioselective rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes: application to the total synthesis of (+)-lasubine II.

Authors:  Robert T Yu; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-09-27       Impact factor: 15.419

6.  Diastereoselective intramolecular temporary silicon-tethered rhodium-catalyzed [4+2+2] cycloisomerization reactions: regiospecific incorporation of substituted 1,3-butadienes.

Authors:  P Andrew Evans; Erich W Baum
Journal:  J Am Chem Soc       Date:  2004-09-15       Impact factor: 15.419

7.  Rhodium catalyzed [4 + 2 + 2] cycloaddition and alkyne insertion: a new route to eight-membered rings.

Authors:  Scott R Gilbertson; Brenton DeBoef
Journal:  J Am Chem Soc       Date:  2002-07-31       Impact factor: 15.419

8.  Total synthesis of indolizidine alkaloid (-)-209D: overriding substrate bias in the asymmetric rhodium-catalyzed [2+2+2] cycloaddition.

Authors:  Robert T Yu; Ernest E Lee; Guillaume Malik; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  The first total synthesis of nakadomarin A.

Authors:  Toshiaki Nagata; Masako Nakagawa; Atsushi Nishida
Journal:  J Am Chem Soc       Date:  2003-06-25       Impact factor: 15.419

10.  Eight-membered ring construction by [4 + 2 + 2] annulation involving beta-carbon elimination.

Authors:  Masahiro Murakami; Shinji Ashida; Takanori Matsuda
Journal:  J Am Chem Soc       Date:  2006-02-22       Impact factor: 15.419
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  10 in total

1.  Phosphoramidite-Rhodium Complexes as Catalysts for the Asymmetric [2+2+2] Cycloaddition of Alkenyl Isocyanates and Alkynes.

Authors:  Rebecca Keller Friedman; Kevin M Oberg; Derek M Dalton; Tomislav Rovis
Journal:  Pure Appl Chem       Date:  2009-07-01       Impact factor: 2.453

2.  An expeditious route to eight-membered heterocycles by nickel-catalyzed cycloaddition: low-temperature C(sp)2-C(sp)3 bond cleavage.

Authors:  Puneet Kumar; Kainan Zhang; Janis Louie
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-17       Impact factor: 15.336

3.  Enantioselective Rhodium-Catalyzed [2+2+2] Cycloaddition of Pentenyl Isocyanate and 4-Ethynylanisole: Preparation and Use of Taddolpyrrolidine Phosphoramidite.

Authors:  Kevin M Oberg; Timothy J Martin; Mark Emil Oinen; Derek M Dalton; Rebecca Keller Friedman; Jamie M Neely; Tomislav Rovis
Journal:  Organic Synth       Date:  2014

4.  Enantioselective rhodium-catalyzed [4+2] cycloaddition of α,β-unsaturated imines and isocyanates.

Authors:  Kevin M Oberg; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2011-03-14       Impact factor: 15.419

5.  Rhodium-catalyzed oxidative cycloaddition of benzamides and alkynes via C-H/N-H activation.

Authors:  Todd K Hyster; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2010-08-04       Impact factor: 15.419

6.  Counterion-Mediated Enantioconvergent Synthesis of Axially Chiral Medium Rings.

Authors:  Ji-Yuan Du; Tudor Balan; Tim D W Claridge; Martin D Smith
Journal:  J Am Chem Soc       Date:  2022-08-03       Impact factor: 16.383

7.  Indole/triazole conjugates are selective inhibitors and inducers of bacterial biofilms.

Authors:  Marine J Minvielle; Cynthia A Bunders; Christian Melander
Journal:  Medchemcomm       Date:  2013-06-01       Impact factor: 3.597

8.  Rhodium-catalyzed C-H functionalization-based approach to eight-membered lactams.

Authors:  Shangze Wu; Rong Zeng; Chunling Fu; Yihua Yu; Xue Zhang; Shengming Ma
Journal:  Chem Sci       Date:  2015-02-05       Impact factor: 9.825

9.  Stereoselective synthesis of medium lactams enabled by metal-free hydroalkoxylation/stereospecific [1,3]-rearrangement.

Authors:  Bo Zhou; Ying-Qi Zhang; Kairui Zhang; Ming-Yang Yang; Yang-Bo Chen; You Li; Qian Peng; Shou-Fei Zhu; Qi-Lin Zhou; Long-Wu Ye
Journal:  Nat Commun       Date:  2019-07-19       Impact factor: 14.919

10.  Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition-Fragmentation Strategy.

Authors:  Megan H Shaw; Rosemary A Croft; William G Whittingham; John F Bower
Journal:  J Am Chem Soc       Date:  2015-06-19       Impact factor: 15.419
  10 in total

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