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1,2- Versus 1,4-Asymmetric Addition of Grignard Reagents to Carbonyl Compounds

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Book cover Progress in Enantioselective Cu(I)-catalyzed Formation of Stereogenic Centers

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 58))

Abstract

The first copper(I)-catalysed conjugate addition of Grignard reagents to α,β-unsaturated carbonyl compounds was reported in 1941. Impressive developments have been made since then, with catalytic asymmetric additions representing the most remarkable achievement. The recent discovery that copper(I) is able to catalyse the asymmetric 1,2-addition of Grignard reagents to α,β-unsaturated, as well as aromatic ketones, was a true revelation. Recent progress in copper(I)-catalysed addition of Grignard reagents is reviewed throughout this chapter, comparing and contrasting the well-established 1,4-selectivity of Cu(I)-ligand complexes with the newly introduced 1,2-selectivity. Mechanistic insights towards the better understanding of the regiodivergence are also discussed.

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Notes

  1. 1.

    In one case, it was possible to carry out the reaction using 60 mol% of titanium tetraisopropoxide Ti(OiPr)4 [81], and in another case it was reported that Ti(OiPr)4-free 1,2-addition to aromatic ketones is possible when a threefold excess of organozinc reagent is used [82].

  2. 2.

    Nakamura et al. predicted an intermediate similar to that of 91, based on theoretical calculations carried out for the addition of organocuprates to acyl chlorides [104].

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  1. Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands

    Pablo Ortiz, Francesco Lanza & Syuzanna R. Harutyunyan

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Ortiz, P., Lanza, F., Harutyunyan, S.R. (2016). 1,2- Versus 1,4-Asymmetric Addition of Grignard Reagents to Carbonyl Compounds. In: Harutyunyan, S. (eds) Progress in Enantioselective Cu(I)-catalyzed Formation of Stereogenic Centers. Topics in Organometallic Chemistry, vol 58. Springer, Cham. https://doi.org/10.1007/3418_2015_164

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