Literature DB >> 20454546

Direct Copper-Free Domino Conjugate Addition-Cycloallylation using Organozinc Reagents.

Venukrishnan Komanduri1, Fernando Pedraza, Michael J Krische.   

Abstract

The Direct Approach: Enones possessing appendant allylic carbonates react directly with diorganozinc reagents in the presence of zinc diiodide [ZnI(2)] to provide 5- and 6-membered ring products of tandem or domino conjugate addition-cycloallylation in good to excellent yield. In a related copper-free transformation, allylic carbonates are found to engage in direct allylic substitution with diorganozinc reagents.

Entities:  

Year:  2008        PMID： 20454546      PMCID： PMC2865154          DOI： 10.1002/adsc.200800242

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  36 in total

1.  Tandem reactions, cascade sequences, and biomimetic strategies in total synthesis.

Authors:  K C Nicolaou; Tamsyn Montagnon; Scott A Snyder
Journal:  Chem Commun (Camb)       Date:  2003-03-07       Impact factor: 6.222

2.  The enantioselective Tsuji allylation.

Authors:  Douglas C Behenna; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419

Review 3.  Catalytic asymmetric tandem transformations triggered by conjugate additions.

Authors:  Hong-Chao Guo; Jun-An Ma
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-09       Impact factor: 15.336

4.  A catalytic asymmetric three-component 1,4-addition/aldol reaction: enantioselective synthesis of the spirocyclic system of vannusal A.

Authors:  K C Nicolaou; Wenjun Tang; Philippe Dagneau; Raffaella Faraoni
Journal:  Angew Chem Int Ed Engl       Date:  2005-06-20       Impact factor: 15.336

5.  Rhodium-catalyzed multicomponent-coupling reactions involving a carborhodation-cross-coupling sequence.

Authors:  Ryo Shintani; Takafumi Yamagami; Tamio Hayashi
Journal:  Org Lett       Date:  2006-10-12       Impact factor: 6.005

6.  Cu-catalyzed asymmetric conjugate additions of alkylzinc reagents to acyclic aliphatic enones.

Authors:  Hirotake Mizutani; Sylvia J Degrado; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2002-02-06       Impact factor: 15.419

7.  Catalytic asymmetric synthesis of acyclic arrays by tandem 1,4-addition-aldol reactions.

Authors:  Gareth P Howell; Stephen P Fletcher; Koen Geurts; Bjorn ter Horst; Ben L Feringa
Journal:  J Am Chem Soc       Date:  2006-11-22       Impact factor: 15.419

8.  Cross-Coupling of Aryl Halides and Allyl Acetates with Arylboron Reagents in Water Using an Amphiphilic Resin-Supported Palladium Catalyst.

Authors:  Yasuhiro Uozumi; Hiroshi Danjo; Tamio Hayashi
Journal:  J Org Chem       Date:  1999-04-30       Impact factor: 4.354

9.  Formation of carbocycles through sequential carborhodation triggered by addition of organoborons.

Authors:  Tomoya Miura; Masahiro Murakami
Journal:  Chem Commun (Camb)       Date:  2006-08-24       Impact factor: 6.222

10.  Cyclization reaction of cyano-substituted unsaturated esters prompted by conjugate addition of organoborons.

Authors:  Tomoya Miura; Tatsuro Harumashi; Masahiro Murakami
Journal:  Org Lett       Date:  2007-02-07       Impact factor: 6.005
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  1 in total

1.  Stereogenic-at-metal Zn- and Al-based N-heterocyclic carbene (NHC) complexes as bifunctional catalysts in Cu-free enantioselective allylic alkylations.

Authors:  Yunmi Lee; Bo Li; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-08-19       Impact factor: 15.419
  1 in total

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