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. 2016:93:210-227.
doi: 10.15227/orgsyn.093.0210.

Preparation of 1,5-Dioxaspiro[5.5]undecan-3-one

Robert A Craig 2nd  1 , Russell C Smith  1 , Beau P Pritchett  1 , Benzi I Estipona  1 , Brian M Stoltz  1
Affiliations

Preparation of 1,5-Dioxaspiro[5.5]undecan-3-one

Robert A Craig 2nd et al. Organic Synth. 2016.

Abstract

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Figures

Figure 1
Figure 1
Transketalization Reaction Set-up
Figure 2
Figure 2
Homogeneous Reaction Mixture at Completion of Transketalization
Figure 3
Figure 3
Distillation Apparatus Before Introduction of Heating and Cooling Baths (baths omitted for visual clarity)
Figure 4
Figure 4
Semi-solid Product After Distillation
Figure 5
Figure 5
Oxidative Cleavage Reaction Set-up Before Cooling
Figure 6
Figure 6
Oxidative Cleavage After Completion Before Quenching
Scheme 1
Scheme 1
Effect of Ketal Identity on Oxidative α-Bromination
Scheme 2
Scheme 2
Removal of Cyclohexyl Ketal Under Relatively Mild Acidic Conditions
See this image and copyright information in PMC

References

    1. Craig RA, II, Roizen JL, Smith RC, Jones AC, Stoltz BM. Org Lett. 2012;14:5716–5719. - PMC - PubMed
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    1. Majewski M, Gleave DM, Nowak P. Can J Chem. 1995;73:1616–1626.
    1. Hoppe D, Schmincke H, Kleemann HW. Tetrahedron. 1989;45:687–694.
    1. Enders D, Bockstiegel B. Synthesis. 1989:493–496.

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