Process for the stereocontrolled silyloxyethylation of azetidino

Details Process for the stereocontrolled silyloxyethylation of azetidino Process for the stereocontrolled silyloxyethylation of azetidino

1988-02-26

1989-03-28

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540360, 540300, 540310, C07F 718, C07F 710, C07B 4102, C07B 4104

Patent

active

048165786

ABSTRACT:
A stereospecific process for preparing 3-trans-R-trisubstituted silyloxyethyl substituted azetidinones useful as intermediates for preparing penems and carbapenems is provided wherein a 3-unsubstituted azetidinone is treated with a strong base and a trisubstituted silylmethyl ketone to form 3-trans-S-[1-trisubstituted silyl-1-hydroxy]ethylazetidinone followed by rearrangement of this resulting carbinol by treatment with an alkali metal alkoxide and a proton source.

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