Prins cyclization heterocycles

Prins cyclization including synthesis of various O- and N-heterocycles 13AA59. 

Overman, L. E., Pennington, L. D. (2003). Strategic Use of Pinacol-Terminated Prins Cyclizations in Target-Oriented Total Synthesis, J. Org. Chem. 68,7143-7157. Taber, D. F. (2006). Stereoselective Construction of Oxygen Heterocycles, Org. Chem. Highlights. 

Olier, C., Kaafarani, M., Gastaldi, S., Bertrand, M. P. (2010). Synthesis of tetrahydropyrans and related heterocycles via prins cyclization extension to aza-prins cyclization. Tetrahedron 66,413 45. 

Dobbs et al carried out the Prins cyclization between homoallylic alcohols, thiols or amines and aldehydes, mediated by InCb [209]. This procedure allowed for the generation of unsaturated heterocycles using mild conditions. Interestingly, for homoallylic amines, the product possesses an anti relative stereochemistry instead of the typical syn observed in most Prins cyclizations (Figure 8.94). 

Fig. 8.94 InCb mediated Prins cyclization for the synthesis of unsaturated heterocycles.

Keywords Annulation Conjugate addition Cyclization Cycloaddition Macrocycles Metathesis Natural products Oxygen-containing heterocycles Prins reaction Spiroketalization... 

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