Literature DB >> 11300884

Origins of stereoselectivity in intramolecular Diels-Alder cycloadditions of dienes and dienophiles linked by ester and amide tethers.

D J Tantillo1, K N Houk, M E Jung.   

Abstract

B3LYP/6-31+G(d) calculations of structures and relative energies for competing transition states for intramolecular Diels-Alder reactions of substituted 3,5-hexadienyl acrylates and acrylamides show that boatlike conformations are sometimes favored in the forming ring that includes the tether.

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Year:  2001        PMID： 11300884     DOI： 10.1021/jo001172h

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  8 in total

1.  Synthesis of the tetracyclic framework of the erythrina alkaloids using a [4 + 2]-cycloaddition/Rh(I)-catalyzed cascade of 2-imidofurans.

Authors:  Albert Padwa; Qiu Wang
Journal:  J Org Chem       Date:  2006-09-15       Impact factor: 4.354

2.  Rhodium(I)-catalyzed nucleophilic ring-opening reactions of oxabicyclo adducts derived from the [4 + 2]-cycloaddition of 2-imido-substituted furans.

Authors:  Albert Padwa; Qiu Wang
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354

3.  An efficient synthesis of (+/-)-Lycoricidine featuring a Stille-IMDAF cycloaddition cascade.

Authors:  Hongjun Zhang; Albert Padwa
Journal:  Org Lett       Date:  2006-01-19       Impact factor: 6.005

4.  Synthesis of some members of the hydroxylated phenanthridone subclass of the Amaryllidaceae alkaloid family.

Authors:  Albert Padwa; Hongjun Zhang
Journal:  J Org Chem       Date:  2007-03-06       Impact factor: 4.354

5.  Origins of regio- and stereochemistry in type 2 intramolecular N-acylnitroso Diels-Alder reactions: a computational study of tether length and substituent effects.

Authors:  Leah Cleary; Victor W Mak; Scott D Rychnovsky; Kenneth J Shea; Nicholas Sizemore
Journal:  J Org Chem       Date:  2013-03-11       Impact factor: 4.354

6.  Synthesis of the erythrina alkaloid 3-demethoxyerythratidinone. Novel acid-induced rearrangements of its precursors.

Authors:  Qiu Wang; Albert Padwa
Journal:  Org Lett       Date:  2006-02-16       Impact factor: 6.005

7.  Tandem cross enyne metathesis (CEYM)-intramolecular Diels-Alder reaction (IMDAR). An easy entry to linear bicyclic scaffolds.

Authors:  Javier Miró; María Sánchez-Roselló; Álvaro Sanz; Fernando Rabasa; Carlos Del Pozo; Santos Fustero
Journal:  Beilstein J Org Chem       Date:  2015-08-25       Impact factor: 2.883

8.  Unusual structure-energy correlations in intramolecular Diels-Alder reaction transition states.

Authors:  Justyna M Zurek; Robert L Rae; Martin J Paterson; Magnus W P Bebbington
Journal:  Molecules       Date:  2014-09-29       Impact factor: 4.411
  8 in total

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