Literature DB >> 20462206

Stereospecific synthesis of alkylidenecyclopropanes via sequential cyclopropene carbomagnesation/1,3-carbon shift.

Xiaocong Xie1, Zhe Yang, Joseph M Fox.   

Abstract

Alkylidenecyclopropanes can be synthesized from enantiomerically enriched cyclopropene derivatives with >99% stereotransfer and good to excellent yield. The protocol comprises the stereoselective reaction of Grignard reagents with 1-alkoxymethyl-3-hydroxymethylcyclopropenes and a stereospecific [1,3] carbon shift reaction.

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Year:  2010        PMID： 20462206      PMCID： PMC2882174          DOI： 10.1021/jo1002938

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


  34 in total

1.  Enantioselective catalytic ring expansion of methylenecyclopropane carboxamides promoted by a chiral magnesium Lewis acid.

Authors:  Catherine Taillier; Mark Lautens
Journal:  Org Lett       Date:  2007-01-25       Impact factor: 6.005

2.  Intramolecular Pauson-Khand reactions of methylenecyclopropane and bicyclopropylidene derivatives as an approach to spiro(cyclopropanebicyclo[n.3.0]alkenones).

Authors:  Armin de Meijere; Heike Becker; Andreas Stolle; Sergei I Kozhushkov; M Teresa Bes; Jacques Salaün; Mathias Noltemeyer
Journal:  Chemistry       Date:  2005-04-08       Impact factor: 5.236

3.  Nickel-catalyzed [3+1+1] cycloaddition reactions of alkenyl Fischer carbene complexes with methylenecyclopropanes.

Authors:  Ken Kamikawa; Yasunori Shimizu; Shin Takemoto; Hiroyuki Matsuzaka
Journal:  Org Lett       Date:  2006-08-31       Impact factor: 6.005

4.  A copper-catalyzed method for the facially selective addition of grignard reagents to cyclopropenes.

Authors:  Lian-An Liao; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2002-12-04       Impact factor: 15.419

5.  Nitrene equivalent mediated metal-free ring expansions of alkylidenecyclopropanes and an alkylidenecyclobutane.

Authors:  Yong Liang; Lei Jiao; Yuanyuan Wang; Yuanyuan Chen; Linge Ma; Jiaxi Xu; Shiwei Zhang; Zhi-Xiang Yu
Journal:  Org Lett       Date:  2006-12-07       Impact factor: 6.005

6.  Theory-guided discovery of unique chemical transformations of cyclopropenes.

Authors:  Robin A Weatherhead-Kloster; E J Corey
Journal:  Org Lett       Date:  2006-01-05       Impact factor: 6.005

7.  Dirhodium(II) tetra(N-(dodecylbenzenesulfonyl)prolinate) catalyzed enantioselective cyclopropenation of alkynes.

Authors:  Huw M L Davies; Gene H Lee
Journal:  Org Lett       Date:  2004-04-15       Impact factor: 6.005

8.  Triplet energy dissipation in methylenecyclopropane rearrangement.

Authors:  Xavier Creary; Andrea Losch; William Sullivan
Journal:  J Org Chem       Date:  2007-09-14       Impact factor: 4.354

9.  A highly site-, regio-, and stereoselective Lewis acid catalyzed formal [3+3] cycloaddition of methylenecyclopropane-1,1-diesters with C,N-diarylnitrones.

Authors:  Bao Hu; Jianlin Zhu; Siyang Xing; Jie Fang; Ding Du; Zhongwen Wang
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

10.  Catalytic regioselectivity control in ring-opening cycloisomerization of methylene- or alkylidenecyclopropyl ketones.

Authors:  Shengming Ma; Lianghua Lu; Junliang Zhang
Journal:  J Am Chem Soc       Date:  2004-08-11       Impact factor: 15.419
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  3 in total

1.  Functionalized Cyclopropenes and Methylenecyclopropenes from Dianions of 3-Hydroxymethylcyclopropenes.

Authors:  Matthew D Hassink; Joseph M Fox
Journal:  Synthesis (Stuttg)       Date:  2012       Impact factor: 3.157

2.  Facially selective Cu-catalyzed carbozincation of cyclopropenes using arylzinc reagents formed by sequential I/Mg/Zn exchange.

Authors:  Vinod Tarwade; Ramajeyam Selvaraj; Joseph M Fox
Journal:  J Org Chem       Date:  2012-10-19       Impact factor: 4.354

3.  Regio- and Diastereoselective Carbometalation Reaction of Cyclopropenes.

Authors:  Yair Cohen; Ilan Marek
Journal:  Acc Chem Res       Date:  2022-09-14       Impact factor: 24.466
  3 in total

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