Literature DB >> 19904370

Asymmetric Au(i)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cycloisomerization process of 1,6-enynes.

Chung-Meng Chao1, Denis Beltrami, Patrick Y Toullec, Véronique Michelet.   

Abstract

The enantioselective asymmetric gold-catalyzed cycloisomerization reactions of heteroatom tethered 1,6-enynes are conducted in the presence of a chiral cationic Au(i) catalyst ((R)-4-MeO-3,5-(t-Bu)(2)-MeOBIPHEP-(AuCl)(2)/AgOTf system) in toluene under mild conditions and lead to functionalized bicyclo[4.1.0]heptene derivatives in excellent enantiomeric excesses ranging from 90-98%.

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Year:  2009        PMID: 19904370     DOI: 10.1039/b913554e

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


  16 in total

1.  Well-Defined Chiral Gold(III) Complex Catalyzed Direct Enantioconvergent Kinetic Resolution of 1,5-Enynes.

Authors:  Patrick T Bohan; F Dean Toste
Journal:  J Am Chem Soc       Date:  2017-08-03       Impact factor: 15.419

2.  Gold(I)-catalyzed diastereo- and enantioselective 1,3-dipolar cycloaddition and Mannich reactions of azlactones.

Authors:  Asa D Melhado; Giovanni W Amarante; Z Jane Wang; Marco Luparia; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-02-22       Impact factor: 15.419

3.  Enantioselective cyclizations of silyloxyenynes catalyzed by cationic metal phosphine complexes.

Authors:  Jean-François Brazeau; Suyan Zhang; Ignacio Colomer; Britton K Corkey; F Dean Toste
Journal:  J Am Chem Soc       Date:  2012-01-31       Impact factor: 15.419

4.  Enantioselective synthesis of cyclic carbamimidates via a three-component reaction of imines, terminal alkynes, and p-toluenesulfonylisocyanate using a monophosphine gold(I) catalyst().

Authors:  Matthew J Campbell; F Dean Toste
Journal:  Chem Sci       Date:  2011-05-12       Impact factor: 9.825

5.  Gold(I)-catalyzed enantioselective polycyclization reactions.

Authors:  Steven G Sethofer; Timo Mayer; F Dean Toste
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

6.  C-C Bond Migration in the Cycloisomerization of 1,6-Enynes.

Authors:  Susan M Stevenson; Eric T Newcomb; Eric M Ferreira
Journal:  Org Chem Front       Date:  2016-06-30       Impact factor: 5.281

7.  Chirality Transfer and Asymmetric Catalysis: Two Strategies toward the Enantioselective Formal Total Synthesis of (+)-Gelsenicine.

Authors:  Phil C Knutson; Haofan Ji; Christopher M Harrington; Yan-Ting Ke; Eric M Ferreira
Journal:  Org Lett       Date:  2022-07-07       Impact factor: 6.072

8.  Cationic gold(I) axially chiral biaryl bisphosphine complex-catalyzed atropselective synthesis of heterobiaryls.

Authors:  Tetsuro Shibuya; Kyosuke Nakamura; Ken Tanaka
Journal:  Beilstein J Org Chem       Date:  2011-07-06       Impact factor: 2.883

9.  Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene.

Authors:  Alexandre Pradal; Chung-Meng Chao; Patrick Y Toullec; Véronique Michelet
Journal:  Beilstein J Org Chem       Date:  2011-07-26       Impact factor: 2.883

10.  Recent advances in the gold-catalyzed additions to C-C multiple bonds.

Authors:  He Huang; Yu Zhou; Hong Liu
Journal:  Beilstein J Org Chem       Date:  2011-07-04       Impact factor: 2.883

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