Facile preparation of allylzinc species from allylboronates and zinc amide via a boron-to-zinc exchange process and their reactions with carbonyl compounds, imines and hydrazones

Cui, Yi; Yamashita, Yasuhiro; Kobayashi, Shū

doi:10.1039/c2cc34340a

Cited by 31 publications

(15 citation statements)

References 42 publications

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“… Allylation with a series of substituted allylboronates. These results have been reported in our communication 16…”

Section: Resultssupporting

confidence: 91%

“… [a] The reaction of 2a (0.40 mmol) with 1a (0.44 mmol) was performed in 0.4 M THF at 20 °C for 3 h in the presence of a zinc catalyst, unless otherwise noted. The results shown in entries 1–7 and 10 have been reported in our communication 16…”

Section: Resultssupporting

confidence: 78%

“…Conditions A: in pentane; conditions B: in pentane‐THF (5:1); conditions C: in pentane‐THF (3:2); conditions D: in THF. The results of product 3b , 3e , 3g–o , 3r , 3s , 3u–w have been reported in our communication 16…”

Section: Resultssupporting

confidence: 74%

“…In this reaction, zinc nucleophiles were formed through transmetalation from boron to zinc. We envisaged that zinc species with stronger conjugate Lewis bases, such as Zn(HMDS) 2 ,15 might have advantages in promoting turnover of zinc species in a catalytic process 16,17. Herein, we report a general catalytic allylation of carbonyl compounds, imines, and hydrazones in the presence of catalytic amounts of Zn(HMDS) 2 .…”

Section: Introductionmentioning

confidence: 99%

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Catalytic Use of Zinc Amide for Transmetalation with Allylboronates: General and Efficient Catalytic Allylation of Carbonyl Compounds, Imines, and Hydrazones

Cui

Sato

et al. 2013

Adv Synth Catal

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The efficient catalytic allylation of ketones, imines, and hydrazones with allylboronates using a catalytic amount of zinc amide is reported. In this reaction, the boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, and the desired allylation reactions proceeded in high efficiency (~0.1 mol%). A mechanistic study revealed that transmetalation was a rate-determining step in the catalytic cycle, and also that the amide ligand on the zinc center played a key role in preparing reactive allylzinc species. Catalytic asymmetric allylations were also investigated, and high enantioselectivities were obtained using chiral di-

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“… Allylation with a series of substituted allylboronates. These results have been reported in our communication 16…”

Section: Resultssupporting

confidence: 91%

Section: Resultssupporting

confidence: 78%

Section: Resultssupporting

confidence: 74%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Catalytic Use of Zinc Amide for Transmetalation with Allylboronates: General and Efficient Catalytic Allylation of Carbonyl Compounds, Imines, and Hydrazones

Cui

Sato

et al. 2013

Adv Synth Catal

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“…[9] Another report, involving aZ n-based catalyst and an allylboronate compound, contains just as ingle example. [10] We were interested in developing am ore general and practical Scheme 1. Is high enantioselectivity feasible without asecond catalystsubstrate contact point?…”

mentioning

confidence: 99%

Practical and Broadly Applicable Catalytic Enantioselective Additions of Allyl‐B(pin) Compounds to Ketones and α‐Ketoesters

et al. 2016

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As et of broadly applicable methods for efficient catalytic additions of easy-to-handle allyl-B(pin) (pin = pinacolato) compounds to ketones and acyclic a-ketoesters was developed. Accordingly,alarge arrayo ft ertiary alcohols can be obtained in 60 to > 98 %yield and up to 99:1 enantiomeric ratio.Atthe heart of this development is rational alteration of the structures of the small-molecule aminophenol-based catalysts.N otably,w ith ketones,i ncreasing the size of ac atalyst moiety (tBu to SiPh 3 )results in muchhigher enantioselectivity. With a-ketoesters,onthe other hand, not only does the opposite hold true,s ince Me substitution leads to substantially higher enantioselectivity,but the sense of the selectivity is reversed as well.

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Organozinc reagents

Ho¹,

Fieser²,

Fieser³

et al. 2017

Fieser and Fieser's Reagents for Organic Synthesis

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Facile preparation of allylzinc species from allylboronates and zinc amide via a boron-to-zinc exchange process and their reactions with carbonyl compounds, imines and hydrazones

Cited by 31 publications

References 42 publications

Catalytic Use of Zinc Amide for Transmetalation with Allylboronates: General and Efficient Catalytic Allylation of Carbonyl Compounds, Imines, and Hydrazones

Catalytic Use of Zinc Amide for Transmetalation with Allylboronates: General and Efficient Catalytic Allylation of Carbonyl Compounds, Imines, and Hydrazones

Practical and Broadly Applicable Catalytic Enantioselective Additions of Allyl‐B(pin) Compounds to Ketones and α‐Ketoesters

Organozinc reagents

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