Literature DB >> 15631443

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

Jian Huang1, Richard P Hsung.   

Abstract

A chiral Lewis acid-catalyzed highly enantioselective [4 + 3] cycloaddition reaction of allenamide-derived nitrogen-stabilized chiral oxyallyl cations is described here. The use of bisoxazoline ligand and CuOTf2 provides high enantioselectivity, especially with [SbF6]- as the counteranion.

Entities:  

Year:  2005        PMID： 15631443     DOI： 10.1021/ja044760b

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


  22 in total

1.  Total synthesis of (±)-rocaglamide via oxidation-initiated Nazarov cyclization.

Authors:  John A Malona; Kevin Cariou; William T Spencer; Alison J Frontier
Journal:  J Org Chem       Date:  2012-01-26       Impact factor: 4.354

2.  Studies on a urea-directed Stork-Crabtree hydrogenation. Synthesis of the C1-C9 subunit of (+)-zincophorin.

Authors:  Zhenlei Song; Richard P Hsung; Ting Lu; Andrew G Lohse
Journal:  J Org Chem       Date:  2007-11-03       Impact factor: 4.354

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

Authors:  Andrew G Lohse; Elizabeth H Krenske; Jennifer E Antoline; K N Houk; Richard P Hsung
Journal:  Org Lett       Date:  2010-11-04       Impact factor: 6.005

4.  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

5.  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

6.  Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis.

Authors:  Steven M Banik; Anna Levina; Alan M Hyde; Eric N Jacobsen
Journal:  Science       Date:  2017-11-10       Impact factor: 47.728

7.  Stereocontrolled Syntheses of Seven-Membered Carbocycles by Tandem Allene Aziridination/[4+3] Reaction.

Authors:  Nels C Gerstner; Christopher S Adams; Maik Tretbar; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

8.  Catalytic asymmetric synthesis of 8-oxabicyclooctanes by intermolecular [5+2] pyrylium cycloadditions.

Authors:  Michael R Witten; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-29       Impact factor: 15.336

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

10.  Saucy-Marbet Rearrangements of Alkynyl Halides in the Synthesis of Highly Enantiomerically Enriched Allenyl Halides.

Authors:  Yu Tang; Lichun Shen; Becky J Dellaria; Richard P Hsung
Journal:  Tetrahedron Lett       Date:  2008-11-03       Impact factor: 2.415
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