Ring Construction of Homoallylic Alcohols and Aldehydes with N-Chlorosuccinimide/Tin(II) Chloride

References

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• 3-Butenyl acetals and/or undetermined products as by-products were obtained in all the reactions.
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• The major diastereomer of 4 (R=C6H5, R'=H) was found to be 2,4-cis 4,6-cis structure by 1H and 13C NMR (Jeolco GX-270) (entry 1 in Table 2).4 The major diastereomer of 4 (R=C6H5, R'=CH3) was also found to be 2,6-cis structure by 13C NMR (entry 2 in Table 2). Thus, the major diastereomer should be 2,4-cis 4,6-cis in all other cases.
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• The reaction of 3 with aliphatic aldehydes such as octanal and 3-phenyl-propanal led to no ring construction under the same reactions as those with aromatic aldehydes.
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