Literature DB >> 12027650

An allenic Pauson-Khand-type reaction: a reversal in pi-bond selectivity and the formation of seven-membered rings.

Kay M Brummond1, Hongfeng Chen, Kimberly D Fisher, Angela D Kerekes, Brenden Rickards, Peter C Sill, Steven J Geib.   

Abstract

[reaction: see text] Treatment of alkynyl allenes with [Rh(CO)(2)Cl](2) results in a formal [2 + 2 + 1] cycloaddition reaction. This reaction occurs with complete regioselectivity for a variety of substrates affording only 4-alkylidene cyclopentenones in good yields. Moreover, seven-membered rings have been prepared in high yields.

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Year:  2002        PMID： 12027650     DOI： 10.1021/ol025955w

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


  11 in total

1.  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

Review 2.  Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

Authors:  Zachary G Brill; Matthew L Condakes; Chi P Ting; Thomas J Maimone
Journal:  Chem Rev       Date:  2017-03-15       Impact factor: 60.622

3.  Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp2)-H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes.

Authors:  Yidong Wang; Sarah G Scrivener; Xiao-Dong Zuo; Ruihan Wang; Philip N Palermo; Ethan Murphy; Austin C Durham; Yi-Ming Wang
Journal:  J Am Chem Soc       Date:  2021-09-07       Impact factor: 16.383

4.  Rh(I)-catalyzed Pauson-Khand-type cycloaddition reaction of ene-vinylidenecyclopropanes with carbon monoxide (CO).

Authors:  Wei Yuan; Xiang Dong; Min Shi; Patrick McDowell; Guigen Li
Journal:  Org Lett       Date:  2012-10-25       Impact factor: 6.005

5.  Conditions for a Rh(I)-catalyzed [2 + 2 + 1] cycloaddition reaction with methyl substituted allenes and alkynes.

Authors:  Sarah M Wells; Kay M Brummond
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

6.  Gold Catalysis-Facilitated Rapid Synthesis of the Daphnane/Tigliane Tricyclic Core.

Authors:  Yong Li; Mufeng Wei; Mingji Dai
Journal:  Tetrahedron       Date:  2016-11-03       Impact factor: 2.457

7.  Controlling, Understanding, and Redirecting the Thermal Rearrangement of 3,3-Dicyano-1,5-enynes.

Authors:  Sarah K Scott; Jacob N Sanders; Katherine E White; Roland A Yu; K N Houk; Alexander J Grenning
Journal:  J Am Chem Soc       Date:  2018-11-12       Impact factor: 15.419

8.  Synthesis of medicinally relevant terpenes: reducing the cost and time of drug discovery.

Authors:  Daniel J Jansen; Ryan A Shenvi
Journal:  Future Med Chem       Date:  2014-06       Impact factor: 3.808

9.  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

10.  The use of silicon-based tethers for the Pauson-Khand reaction.

Authors:  Adrian P Dobbs; Ian J Miller; Sasa Martinović
Journal:  Beilstein J Org Chem       Date:  2007-07-06       Impact factor: 2.883
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