Diastereoselective synthesis of (1S,2S,3R,6S) 3-chloro-3-methyl-6-isopropenyl-1,2-cyclohexanediol via Prins reaction induced by zinc and trimethylsilyl chloride

DOI: 10.1016/0040-4020(96)00167-6

Source and publish data:

Tetrahedron p. 4645 - 4658 (1996)

Update date:2022-07-29

Topics:

Authors:

Marty, Maurus

Stoeckli-Evans, Helen

Neier, Reinhard

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Article abstract of DOI:10.1016/0040-4020(96)00167-6

While attempting to synthesize a potential inhibitor of the biosynthesis step of formation of PBG, a novel catalytic system inducing the Prins reaction was discovered. Treatment of epoxy geranial with Zn and trimethylsilyl chloride gave (1S,2S,3R,6S) 3-Chloro-3-methyl-6-isopropenyl-1,2-cyclohexanediol in high diastereoselectivity.

Full text of DOI:10.1016/0040-4020(96)00167-6

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