Literature DB >> 21666901

Control of selectivity in the generation and reactions of oxonium ylides.

Deana M Jaber1, Ryan N Burgin, Matthew Hepler, Peter Zavalij, Michael P Doyle.   

Abstract

Dirhodium catalyzed reactions of aryl-substituted tetrahydropyranone diazoacetoacetates produce ylide intermediates that unexpectedly yield two oxabicyclo[4.2.1]-nonane diastereoisomers, but a single diastereoisomer is formed by increasing the steric bulk of the aryl substituent.

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Year:  2011        PMID： 21666901     DOI： 10.1039/c1cc12443a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  7 in total

1.  Competitive [2,3]- and [1,2]-oxonium ylide rearrangements. Concerted or stepwise?

Authors:  Deana M Jaber; Ryan N Burgin; Matthew Helper; Peter Y Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2012-03-12       Impact factor: 6.005

2.  Substrate-dependent divergent outcomes from catalytic reactions of silyl-protected enol diazoacetates with nitrile oxides: azabicyclo[3.1.0]hexanes or 5-arylaminofuran-2(3H)-ones.

Authors:  Xinfang Xu; Dmitry Shabashov; Peter Y Zavalij; Michael P Doyle
Journal:  J Org Chem       Date:  2012-06-04       Impact factor: 4.354

Review 3.  Cycloaddition reactions of enoldiazo compounds.

Authors:  Qing-Qing Cheng; Yongming Deng; Marianne Lankelma; Michael P Doyle
Journal:  Chem Soc Rev       Date:  2017-08-29       Impact factor: 54.564

4.  Functionalizing the γ-Position of α-Diazo-β-ketoesters.

Authors:  Thu Q Nguyen; Maha Alqurafi; Cash Edwards; Pauline Nguyen; Jean Kim; Samuel Casco; Maricka Bennet; Christopher Chiang; Maureen Lohry; Melina Cox; Byron Meshram; Duyen Le; Eugene Kim; Snigdha Smriti; Peter Oelschlaeger; John D Buynak
Journal:  Tetrahedron Lett       Date:  2016-06-16       Impact factor: 2.415

5.  Photochemical ring expansion reactions: synthesis of tetrahydrofuran derivatives and mechanism studies.

Authors:  Sripati Jana; Zhen Yang; Chao Pei; Xinfang Xu; Rene M Koenigs
Journal:  Chem Sci       Date:  2019-09-06       Impact factor: 9.825

6.  Asymmetric synthesis of isochromanone derivatives via trapping carboxylic oxonium ylides and aldol cascade.

Authors:  Jiawen Lang; Siyuan Wang; Changli He; Xiaohua Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2021-12-27       Impact factor: 9.825

7.  Rh2(II)-catalyzed selective aminomethylene migration from styryl azides.

Authors:  Chen Kong; Navendu Jana; Tom G Driver
Journal:  Org Lett       Date:  2013-02-04       Impact factor: 6.005
  7 in total

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