Diastereoselective process leading to a key intermediate for the

Details Diastereoselective process leading to a key intermediate for the Diastereoselective process leading to a key intermediate for the

1994-01-31

1996-03-12

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548186, 549454, 549475, C07D41306

Patent

active

054987199

ABSTRACT:
The present invention provides a novel synthetic route to a key precursor, i.e., an (S,S)-.alpha.-fluoro-2,2-dimethyl-1,3-dioxolane-4-propanoic acid ester useful in the preparation of FddA and FddC. The instant diastereoselective process utilizes a novel intermediate which contains a chiral auxiliary. The chiral auxiliary can be any chiral auxiliary moiety such as for example an auxiliary containing a substituted oxazolidinone group. The intermediate containing the chiral auxiliary is fluorinated utilizing a fluorination method applied for the first time in the synthesis of fluorinated sugars to give a fluorinated intermediate which after removal of the chiral group provides the desired key intermediate. In summary, in the instant process, a fluorine is introduced diastereoselectively into an intermediate via the reaction of a chiral enolate with an electrophilic fluorinating agent and the intermediate which is fluorinated is derived from mannitol.

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