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Synthesis 2005(18): 2995-3022
DOI: 10.1055/s-2005-918455
DOI: 10.1055/s-2005-918455
REVIEW
© Georg Thieme Verlag Stuttgart · New York
A Concise Account of Recent SN2′ Grignard Coupling Reactions in Organic Synthesis [1]
Weitere Informationen
Received
19 May 2005
Publikationsdatum:
28. Oktober 2005 (online)
Publikationsverlauf
Publikationsdatum:
28. Oktober 2005 (online)
Abstract
Over the past few decades studies on controlling the chemo-, regio- and stereoselectivities of allylic substitution reactions have been well documented in the literature and the SN2′ Grignard coupling reaction has emerged as a very powerful tool in selective carbon-carbon bond formation. This review focuses on all the recent synthetic developments in this special class of reactions.
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1 Introduction
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2 SN2′ Grignard Coupling Reactions with Allylic Substrates
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2.1 Allyl Halides
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2.2 Allyl Acetates
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2.3 Allyl Carbonates
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2.4 Allyl Carbamates
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2.5 Allyl Ethers
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2.6 Allyl Silyl Ethers
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2.7 Allyl Epoxides
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2.8 Allyl Aziridines
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2.9 Allyl Oxazolidinones
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2.10 Allyl Thioethers
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2.11 Allyl Benzotriazoles
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2.12 Oxabicyclic Alkenes
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2.13 Azabicyclic Alkenes
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2.14 Oxa-azabicyclic Alkenes
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3 SN2′ Grignard Coupling Reactions with Propargyl Substrates
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3.1 Propargyl Acetates
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3.2 Propargyl Silyl Ethers
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3.3 Propargyl Epoxides
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3.4 Propargyl Aziridines
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3.5 Propargyl Dithioacetals
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3.6 Propargyl Thioethers
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4 SN2′ Grignard Coupling Reactions with Bromoallenes
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5 SN2′ Grignard Coupling Reactions in Natural/Unnatural Product Synthesis
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6 Conclusions
Key words
chiral/achiral SN2′ Grignard coupling reactions - allylic substrates - propargyl substrates - bromoallenes - natural products
NCL Communication No. 6683.
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NCL Communication No. 6683.