Literature DB >> 23170869

Lewis acid catalyzed intramolecular condensation of ynol ether-acetals. Synthesis of alkoxycycloalkene carboxylates.

Vincent Tran1, Thomas G Minehan.   

Abstract

Treatment of ynol ether-tethered dialkyl acetals with catalytic quantities of scandium triflate in CH(3)CN gives rise to five-, six-, and seven-membered alkoxycycloalkene carboxylates in good to excellent yields. Tri- and tetrasubstituted carbocyclic and heterocyclic alkenes may be formed by this method, and the products obtained may serve as useful intermediates for natural product synthesis.

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Year:  2012        PMID： 23170869      PMCID： PMC3518682          DOI： 10.1021/ol303026v

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


  12 in total

1.  The total synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalyzed rearrangement of α,β-unsaturated enol esters.

Authors:  Lisa Candish; David W Lupton
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

2.  The Meyer-Schuster rearrangement for the synthesis of alpha,beta-unsaturated carbonyl compounds.

Authors:  Douglas A Engel; Gregory B Dudley
Journal:  Org Biomol Chem       Date:  2009-09-14       Impact factor: 3.876

3.  Intramolecular [2 + 2] cycloaddition reactions of alkynyl ether derived ketenes. A convenient synthesis of donor-acceptor cyclobutanes.

Authors:  Vincent Tran; Thomas G Minehan
Journal:  Org Lett       Date:  2011-11-21       Impact factor: 6.005

4.  A ring-closing yne-carbonyl metathesis of ynamides.

Authors:  Kimberly C M Kurtz; Richard P Hsung; Yanshi Zhang
Journal:  Org Lett       Date:  2006-01-19       Impact factor: 6.005

5.  Total synthesis and determination of the absolute configuration of (-)-idesolide.

Authors:  Hiroyuki Yamakoshi; Masatoshi Shibuya; Masaki Tomizawa; Yuji Osada; Naoki Kanoh; Yoshiharu Iwabuchi
Journal:  Org Lett       Date:  2010-03-05       Impact factor: 6.005

6.  Highly efficient chemoselective deprotection of O,O-acetals and O,O-ketals catalyzed by molecular iodine in acetone.

Authors:  Jianwei Sun; Yanmei Dong; Liya Cao; Xinyan Wang; Shaozhong Wang; Yuefei Hu
Journal:  J Org Chem       Date:  2004-12-10       Impact factor: 4.354

7.  Stereoselective synthesis of (E)-2-en-4-ynoic acids with ynolates: catalytic conversion to tetronic acids and 2-pyrones.

Authors:  Takashi Yoshikawa; Mitsuru Shindo
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005

8.  Synthesis of amides and lactams in supercritical carbon dioxide.

Authors:  Xiao Yin Mak; Rocco P Ciccolini; Julia M Robinson; Jefferson W Tester; Rick L Danheiser
Journal:  J Org Chem       Date:  2009-12-18       Impact factor: 4.354

9.  Indium(III) trifluoromethanesulfonate as an efficient catalyst for the deprotection of acetals and ketals.

Authors:  Brian T Gregg; Kathryn C Golden; John F Quinn
Journal:  J Org Chem       Date:  2007-06-27       Impact factor: 4.354

10.  Reactive intermediates from DMDO oxidation of ynamides. Trapping of a de novo chiral push-pull carbene via cyclopropanation.

Authors:  Ziyad F Al-Rashid; Richard P Hsung
Journal:  Org Lett       Date:  2008-01-17       Impact factor: 6.005
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  2 in total

1.  A Single-Flask Synthesis of α-Alkylidene and α-Benzylidene Lactones from Ethoxyacetylene, Epoxides/Oxetanes, and Carbonyl Compounds.

Authors:  Kevin Ng; Vincent Tran; Thomas Minehan
Journal:  Tetrahedron Lett       Date:  2016-01-20       Impact factor: 2.415

2.  Copper-catalyzed radical trans-selective hydroboration of ynamides with N-heterocyclic carbene boranes.

Authors:  Kefeng Wang; Qingzhen Yu; Wenli Mao; Yuxin Zheng; Jing Xu; Yukun Wang
Journal:  iScience       Date:  2022-08-17
  2 in total

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