Organocatalytic Asymmetric Direct CH Functionalization of Ethers: A Highly Efficient Approach to Chiral Spiroethers

Jiao, Zhiwei; Zhang, Shuyu; He, Chuan; Tu, Yong‐Qiang; Wang, Shaohua; Zhang, Fu‐Min; Zhang, Yongqiang; Li, Hui

doi:10.1002/ange.201204274

Cited by 32 publications

(8 citation statements)

References 89 publications

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“…More recently, Tu and co‐workers successfully achieved the enantioselective 1,5‐hydride‐shift/cyclization reaction of racemic cyclic ethers 61 (Scheme ) 34. Impressive levels of diastereoselectivity were attained in this transformation.…”

Section: Enantioselective 15‐hydride‐shift Processesmentioning

confidence: 99%

The Redox‐Neutral Approach to CH Functionalization

Peng

Maulide

2013

Chemistry A European J

289

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The direct functionalization of C-H bonds is an attractive strategy in organic synthesis. Although several advances have been made in this area, the selective activation of inert sp(3) C-H bonds remains a daunting challenge. Recently, a new type of sp(3) C-H activation mode through internal hydride transfer has demonstrated the potential to activate remote sp(3) C-H linkages in an atom-economic manner. This Minireview attempts to classify recent advances in this area including the transition to non-activated sp(3) C-H bonds and asymmetric hydride transfers.

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Section: Enantioselective 15‐hydride‐shift Processesmentioning

confidence: 99%

The Redox‐Neutral Approach to CH Functionalization

Peng

Maulide

2013

Chemistry A European J

289

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“…62%—87% yields, up to 94/6 dr and up to 96% ee (Scheme 1a). [ 5a ] In 2006, Yadav and co‐workers demonstrated that Lewis acid catalyzed [3+2] annulation of silylmethylcyclopropanes with cyclohexanone could provide a facile access to the racemic 1‐oxaspiro[4.5]decane (Scheme 1a). [6a] In 2012, Waser and co‐workers reported a catalytic enantiospecific [3+2] annulation of aminocyclopropanes with cyclohexanone, where enantioenriched cyclo‐…”

Section: Background and Originality Contentmentioning

confidence: 99%

Asymmetric Catalytic [3+2] Annulation of Donor‐Acceptor Cyclopropane with Cyclic Ketones: Facile Access to Enantioenriched 1‐Oxaspiro[4.5]decanes^†

et al. 2020

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of main observation and conclusion A copper catalyzed enantioselective [3+2] annulation of donor-acceptor cyclopropanes with cyclic ketones has been developed, providing a concise protocol to enantioenriched 1-oxaspiro[4.5]decanes in up to 98% yield with up to >99/1 dr and up to 92% ee. In addition, this method also provides a facile access to the enantioselective desymmetrisation of various 4-substituted cyclohexanones. The resulting products were easily converted to the core structures of two natural products Heliespirones A and halogenated sesquiterpene isolated from L. saitoi.

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“…In 2012, Tu and co‐workers reported a Macmillan catalyst 160 ‐catalyzed asymmetric α‐alkylation of tetrahydrofuran 158 containing an α,β‐unsaturated aldehyde to construct the chiral spiroether 159 (Scheme ) 52. The sequential [1,5]‐hydride transfer/cyclization was facilitated via a cascade iminium/enamine activation.…”

Section: C(sp3)h Bonds Adjacent To Ethereal Oxygenmentioning

confidence: 99%

Dielectric Relaxation Studies of Binary Mixture of α‐Picoline and Methanol Using Time Domain Reflectometry at Different Temperatures

Trivedi

Rana

Hudge³

et al. 2015

J Chinese Chemical Soc

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Complex permittivity spectra of binary mixtures of varying concentrations of α‐picoline and methanol (MeOH) were obtained using time domain reflectometry (TDR) technique over frequency range 10 MHz to 25 GHz at 283.15 K, 288.15 K, 293.15 K and 298.15 K temperatures. The dielectric relaxation parame‐ ters namely static permittivity (σ0), high frequency limit permittivity (σoo1) and the relaxation time (ρ) were determined by fitting complex permittivity data to the single Debye/Cole‐Davidson model. Complex non linear least square (CNLS) fitting procedure was carried out using LEVMW software. The excess static permittivity (σ0E) and the excess inverse relaxation time (1/ρ)E which contains information regarding mo‐ lecular structure and interaction between polar — polar liquids, were also determined. From the experimental data, effective Kirkwood correlation factor (geff) and Bruggeman factor (fB) were calculated. Excess parameters were fitted to the Redlich‐Kister polynomial equation. The values of static permittivity and relaxation time increase non‐linearly with increase in the mol fraction of MeOH at all temperatures. The values of excess static permittivity (σ0E) and the excess inverse relaxation time (1/ρ)E are negative for the studied α‐picoline — MeOH system at all temperatures.

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Organocatalytic Asymmetric Direct CH Functionalization of Ethers: A Highly Efficient Approach to Chiral Spiroethers

Cited by 32 publications

References 89 publications

The Redox‐Neutral Approach to CH Functionalization

The Redox‐Neutral Approach to CH Functionalization

Asymmetric Catalytic [3+2] Annulation of Donor‐Acceptor Cyclopropane with Cyclic Ketones: Facile Access to Enantioenriched 1‐Oxaspiro[4.5]decanes^†

Dielectric Relaxation Studies of Binary Mixture of α‐Picoline and Methanol Using Time Domain Reflectometry at Different Temperatures

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Organocatalytic Asymmetric Direct CH Functionalization of Ethers: A Highly Efficient Approach to Chiral Spiroethers

Cited by 32 publications

References 89 publications

The Redox‐Neutral Approach to CH Functionalization

The Redox‐Neutral Approach to CH Functionalization

Asymmetric Catalytic [3+2] Annulation of Donor‐Acceptor Cyclopropane with Cyclic Ketones: Facile Access to Enantioenriched 1‐Oxaspiro[4.5]decanes†

Dielectric Relaxation Studies of Binary Mixture of α‐Picoline and Methanol Using Time Domain Reflectometry at Different Temperatures

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Asymmetric Catalytic [3+2] Annulation of Donor‐Acceptor Cyclopropane with Cyclic Ketones: Facile Access to Enantioenriched 1‐Oxaspiro[4.5]decanes^†