Organic Letters 2005-06-09

2-Ene-1,4-diols by dimerization of terminal epoxides using hindered lithium amides.

David M Hodgson, Christopher D Bray, Nicholas D Kindon

Index: Org. Lett. 7(12) , 2305-8, (2005)

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Abstract

[reaction: see text] Reaction of hindered lithium amides with readily available (enantiopure) terminal epoxides gives 2-ene-1,4-diols via carbenoid dimerization of the corresponding alpha-lithiated epoxides. D-Mannitol and D-iditol were synthesized using this method in three steps from (S)-tritylglycidyl ether.

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