A Concise Account of Recent SN2′ Grignard Coupling Reactions in Organic Synthesis

Anirban Kar; Narshinha P. Argade

doi:10.1055/s-2005-918455

REVIEW

A Concise Account of Recent S_N2′ Grignard Coupling Reactions in Organic Synthesis [1]

Anirban Kar*, Narshinha P. Argade*
Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India
Fax: +91(20)25893153; e-Mail: np.argade@ncl.res.in;

Abstract

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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 S_N2′ 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.

1 Introduction
2 S_N2′ Grignard Coupling Reactions with Allylic Substrates
2.1 Allyl Halides
2.2 Allyl Acetates
2.3 Allyl Carbonates
2.4 Allyl Carbamates
2.5 Allyl Ethers
2.6 Allyl Silyl Ethers
2.7 Allyl Epoxides
2.8 Allyl Aziridines
2.9 Allyl Oxazolidinones
2.10 Allyl Thioethers
2.11 Allyl Benzotriazoles
2.12 Oxabicyclic Alkenes
2.13 Azabicyclic Alkenes
2.14 Oxa-azabicyclic Alkenes
3 S_N2′ Grignard Coupling Reactions with Propargyl Substrates
3.1 Propargyl Acetates
3.2 Propargyl Silyl Ethers
3.3 Propargyl Epoxides
3.4 Propargyl Aziridines
3.5 Propargyl Dithioacetals
3.6 Propargyl Thioethers
4 S_N2′ Grignard Coupling Reactions with Bromoallenes
5 S_N2′ Grignard Coupling Reactions in Natural/Unnatural Product Synthesis
6 Conclusions

Key words

chiral/achiral S_N2′ Grignard coupling reactions - allylic substrates - propargyl substrates - bromoallenes - natural products

Full Text

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A Concise Account of Recent SN2′ Grignard Coupling Reactions in Organic Synthesis [1]

A Concise Account of Recent S_N2′ Grignard Coupling Reactions in Organic Synthesis [1]