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Synlett 1991; 1991(8): 539-547
DOI: 10.1055/s-1991-20790
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New Tools in Synthetic Organocopper Chemistry

Eiichi Nakamura*
  • *Department of Chemistry, Tokyo Institute of Technology, Meguro, Tokyo 152, Japan
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Publication Date:
07 March 2002 (online)

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A variety of organocopper reactions including chlorotrimethylsilane-accelerated conjugate addition, regio- and diastereoselective SN2′-allylation reaction, and asymmetric carbocupration reaction are reviewed with emphasis on the results from author's own laboratories. 1. Introduction 2. Chlorosilane-Accelerated Conjugate Additions 2.1. Copper Homoenolate 2.2. Stoichiometric and Catalytic Copper Reagents 3. Chemoselectivity of Organocopper Reagents: A Zinc/Copper Combination 3.1. Metal Homoenolate Chemistry 3.2. Functionalized Copper Reagents 4. SN2′-Selective Allylation Reaction and its Diastereoselectivity 4.1. 1,2-Asymmetric Induction 4.2. A d-π* Model 5. A New Reaction: Asymmetric Carbocupration Reaction 5.1. Synthesis of Substituted Cyclopropenone Acetals 5.2. Carbocupration of Cyclopropenone Acetals 5.3. Asymmetric Carbocupration of Cyclopropenone Acetals

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