Literature DB >> 21049917

Regioselectivities of (4 + 3) cycloadditions between furans and oxazolidinone-substituted oxyallyls.

Andrew G Lohse1, Elizabeth H Krenske, Jennifer E Antoline, K N Houk, Richard P Hsung.   

Abstract

The (4 + 3) cycloadditions of oxazolidinone-substituted oxyallyls and unsymmetrically substituted furans lead to syn regioselectivity when the furan has a 2-Me or 2-COOR substituent, while anti regioselectivity is obtained with a 3-Me or 3-COOR group. DFT calculations are performed to explain the selectivities. The reactivities and regioselectivities are consistent with the ambiphilic reactivity of amino-oxyallyls with furans.

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Year:  2010        PMID： 21049917      PMCID： PMC2993829          DOI： 10.1021/ol1023745

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


  23 in total

1.  Intramolecular 4 + 3 cycloadditions. A theoretical analysis of simple diastereoselectivity in reactions of alkoxyallylic cations and furans.

Authors:  M Harmata; P R Schreiner
Journal:  Org Lett       Date:  2001-11-15       Impact factor: 6.005

2.  Intramolecular 4 + 3 cycloadditions. Theoretical and experimental evaluation of endo/exo preferences of a cyclopentenyl cation.

Authors:  C J Cramer; M Harmata; P Rashatasakhon
Journal:  J Org Chem       Date:  2001-08-10       Impact factor: 4.354

3.  8-Oxabicyclo[3.2.1]oct-6-en-3-ones: application to the asymmetric synthesis of polyoxygenated building blocks.

Authors:  Ingo V Hartung; H Martin R Hoffmann
Journal:  Angew Chem Int Ed Engl       Date:  2004-04-02       Impact factor: 15.336

Review 4.  Exploration of fundamental and synthetic aspects of the intramolecular 4 + 3 cycloaddition reaction.

Authors:  M Harmata
Journal:  Acc Chem Res       Date:  2001-07       Impact factor: 22.384

5.  Chiral Lewis acid-catalyzed highly enantioselective [4 + 3] cycloaddition reactions of nitrogen-stabilized oxyallyl cations derived from allenamides.

Authors:  Jian Huang; Richard P Hsung
Journal:  J Am Chem Soc       Date:  2005-01-12       Impact factor: 15.419

6.  Asymmetric organocatalysis of 4 + 3 cycloaddition reactions.

Authors:  Michael Harmata; Sunil K Ghosh; Xuechuan Hong; Sumrit Wacharasindhu; Patrick Kirchhoefer
Journal:  J Am Chem Soc       Date:  2003-02-26       Impact factor: 15.419

7.  Ligand-controlled regioselectivity in palladium-catalyzed cross coupling reactions.

Authors:  Franziska Schoenebeck; K N Houk
Journal:  J Am Chem Soc       Date:  2010-03-03       Impact factor: 15.419

8.  Inter- and intramolecular [4 + 3] cycloadditions using epoxy enol silanes as functionalized oxyallyl cation precursors.

Authors:  Wing Ki Chung; Sze Kui Lam; Brian Lo; Lok Lok Liu; Wing-Tak Wong; Pauline Chiu
Journal:  J Am Chem Soc       Date:  2009-04-08       Impact factor: 15.419

9.  Understanding the nature of the molecular mechanisms associated with the competitive Lewis acid catalyzed [4+2] and [4+3] cycloadditions between arylidenoxazolone systems and cyclopentadiene: a DFT analysis.

Authors:  Manuel Arnó; M Teresa Picher; Luis R Domingo; Juan Andrés
Journal:  Chemistry       Date:  2004-10-04       Impact factor: 5.236

10.  A tandem epoxidation/stereoselective intramolecular [4+3] cycloaddition reaction involving nitrogen-stabilized oxyallyl cations derived from chiral allenamides.

Authors:  Challeppan Rameshkumar; Richard P Hsung
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-01       Impact factor: 15.336
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  15 in total

1.  Stereoselective 6π-electron electrocyclic ring closures of 2-halo-amidotrienes via a remote 1,6-asymmetric induction.

Authors:  Ryuji Hayashi; Mary C Walton; Richard P Hsung; John H Schwab; Xueliang Yu
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

2.  Aromatic interactions as control elements in stereoselective organic reactions.

Authors:  Elizabeth H Krenske; K N Houk
Journal:  Acc Chem Res       Date:  2012-07-24       Impact factor: 22.384

3.  Intramolecular oxyallyl-carbonyl (3 + 2) cycloadditions.

Authors:  Elizabeth H Krenske; Shuzhong He; Jian Huang; Yunfei Du; K N Houk; Richard P Hsung
Journal:  J Am Chem Soc       Date:  2013-04-01       Impact factor: 15.419

4.  Generation and Reactivity of 2-Amido-1,3-diaminoallyl Cations: Cyclic Guanidine Annulations via Net (3 + 2) and (4 + 3) Cycloadditions.

Authors:  V Raghavendra Rao Kovvuri; Haoran Xue; Daniel Romo
Journal:  Org Lett       Date:  2020-02-03       Impact factor: 6.005

5.  Oppolzer-type intramolecular Diels-Alder cycloadditions via isomerizations of allenamides.

Authors:  John B Feltenberger; Richard P Hsung
Journal:  Org Lett       Date:  2011-05-25       Impact factor: 6.005

6.  Developing a diastereoselective intramolecular [4+3] cycloaddition of nitrogen-stabilized oxyallyl cations derived from N-sulfonyl-substituted allenamides.

Authors:  Andrew G Lohse; Richard P Hsung; Mitchell D Leider; Sunil K Ghosh
Journal:  J Org Chem       Date:  2011-04-08       Impact factor: 4.354

7.  Highly torquoselective electrocyclizations and competing 1,7-hydrogen shifts of 1-azatrienes with silyl substitution at the allylic carbon.

Authors:  Zhi-Xiong Ma; Ashay Patel; K N Houk; Richard P Hsung
Journal:  Org Lett       Date:  2015-04-10       Impact factor: 6.005

8.  Stereoselectivities and regioselectivities of (4 + 3) cycloadditions between allenamide-derived chiral oxazolidinone-stabilized oxyallyls and furans: experiment and theory.

Authors:  Jennifer E Antoline; Elizabeth H Krenske; Andrew G Lohse; K N Houk; Richard P Hsung
Journal:  J Am Chem Soc       Date:  2011-08-18       Impact factor: 15.419

9.  Control of regioselectivity and stereoselectivity in (4 + 3) cycloadditions of chiral oxyallyls with unsymmetrically disubstituted furans.

Authors:  Yunfei Du; Elizabeth H Krenske; Jennifer E Antoline; Andrew G Lohse; K N Houk; Richard P Hsung
Journal:  J Org Chem       Date:  2012-07-31       Impact factor: 4.354

Review 10.  Allenamides: a powerful and versatile building block in organic synthesis.

Authors:  Ting Lu; Zhenjie Lu; Zhi-Xiong Ma; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2013-04-04       Impact factor: 60.622
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