Literature DB >> 22409577

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

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

Abstract

The axial-equatorial conformational isomer distribution of the reactant diazoacetoacetate or its metal carbene intermediate is reflected in Rh(II) catalyzed oxonium ylide forming reactions of 3-(trans-2-arylvinyl)tetrahydropyranone-5-diazoacetoacetates that afford diastereoisomeric products for both the symmetry-allowed [2,3]- and the formally symmetry-forbidden [1,2]-oxonium ylide rearrangements.

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Year:  2012        PMID： 22409577      PMCID： PMC3321102          DOI： 10.1021/ol300213u

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


  17 in total

1.  Recent Advances in Asymmetric Catalytic Metal Carbene Transformations.

Authors:  Michael P. Doyle; David C. Forbes
Journal:  Chem Rev       Date:  1998-04-02       Impact factor: 60.622

2.  Linear free energy correlation analysis on the electronic effects of Rh(II) carbene O-H insertion.

Authors:  Zhaohui Qu; Weifeng Shi; Jianbo Wang
Journal:  J Org Chem       Date:  2004-01-09       Impact factor: 4.354

3.  Electronic effects in migratory groups. [1,4]-versus[1,2]-rearrangement in rhodium carbenoid generated bicyclic oxonium ylides.

Authors:  N P Karche; S M Jachak; D D Dhavale
Journal:  J Org Chem       Date:  2001-09-21       Impact factor: 4.354

4.  Hydrazulene ring systems via heteroatom-assisted [1,2]-shift of oxonium and sulfonium ylides.

Authors:  Graham K Murphy; F G West
Journal:  Org Lett       Date:  2005-04-28       Impact factor: 6.005

5.  Iterative approach to polycyclic ethers based on stereoselective oxonium ylide [2,3]-shifts.

Authors:  F P Marmsäter; F G West
Journal:  J Am Chem Soc       Date:  2001-05-30       Impact factor: 15.419

6.  Alkynyliodonium salts in organic synthesis. Dihydrofuran formation via a formal stevens shift of a carbon substituent within a disubstituted-carbon oxonium ylide.

Authors:  K S Feldman; M L Wrobleski
Journal:  J Org Chem       Date:  2000-12-15       Impact factor: 4.354

7.  Expedient route to the tigliane-daphnane skeleton via oxonium ylide [1,2]-shift.

Authors:  Craig Stewart; Robert McDonald; F G West
Journal:  Org Lett       Date:  2011-01-11       Impact factor: 6.005

8.  Carbon-carbon bond formation reaction of ethereal oxonium ylides via metal-enolate intermediates.

Authors:  Yuichi Sawada; Takashi Mori; Akira Oku
Journal:  J Org Chem       Date:  2003-12-26       Impact factor: 4.354

9.  Asymmetric Lewis acid mediated [1,2]-rearrangement of proline-derived ammonium ylides.

Authors:  Pavel Tuzina; Peter Somfai
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

10.  Catalyst and ring size effects on periselectivity of oxonium ylide rearrangements.

Authors:  Fredrik P Marmsäter; John A Vanecko; F G West
Journal:  Org Lett       Date:  2004-05-13       Impact factor: 6.005
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  8 in total

1.  Aziridinium Ylides: Underutilized Intermediates for Complex Amine Synthesis.

Authors:  Hillary J Dequina; Jennifer M Schomaker
Journal:  Trends Chem       Date:  2020-09-02

2.  Highly stereoselective C-C bond formation by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and chiral allylic alcohols.

Authors:  Zhanjie Li; Brendan T Parr; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2012-06-25       Impact factor: 15.419

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.  Highly selective catalyst-dependent competitive 1,2-C→C, -O→C, and -N→C migrations from β-methylene-β-silyloxy-β-amido-α-diazoacetates.

Authors:  Xichen Xu; Yu Qian; Peter Y Zavalij; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2013-01-17       Impact factor: 15.419

5.  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

6.  Ring Expansion of Bicyclic Methyleneaziridines via Concerted, Near-Barrierless [2,3]-Stevens Rearrangements of Aziridinium Ylides.

Authors:  Steven C Schmid; Ilia A Guzei; Israel Fernández; Jennifer M Schomaker
Journal:  ACS Catal       Date:  2018-07-17       Impact factor: 13.084

7.  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

8.  Dynamics and a unified understanding of competitive [2,3]- and [1,2]-sigmatropic rearrangements based on a study of ammonium ylides.

Authors:  Bibaswan Biswas; Sean C Collins; Daniel A Singleton
Journal:  J Am Chem Soc       Date:  2014-02-28       Impact factor: 15.419
  8 in total

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