Silyl enol ether alkylation process

Details Silyl enol ether alkylation process Silyl enol ether alkylation process

1995-06-02

1998-02-17

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20508, C07D22700, C07D48704, C07D49904

Patent

active

057192758

ABSTRACT:
A method for preparing compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen or a hydroxy-protecting group; R.sup.2 is alkyl, alkoxy, halogen, optionally substituted phenyl or optionally substituted phenoxy; R.sup.3 is optionally substituted pyridyl, optionally substituted quinolyl or phenyl group which has a substituent of formula --CYNR.sup.5 R.sup.6, where Y is oxygen or sulfur, and R.sup.5 and R.sup.6 are each alkyl, aryl or aralkyl, or R.sup.5 and R.sup.6 and the nitrogen to which they are attached together form a heterocyclic group; R.sup.4 is hydrogen or an amino-protecting group; and Z is sulfur or oxygen. The process comprises reacting a compound of formula (II): ##STR2## in which R.sup.8, R.sup.9 and R.sup.10 are the same or different and each represents an alkyl group having from 1 to 4 carbon atoms or a phenyl group, with a compound of formula (III): ##STR3## in which R.sup.11 represents an acyloxy, alkylsulfonyl, arylsulfonyl, alkylsulfinyl or arylsulfinyl group.

REFERENCES:
patent: 4772683 (1988-09-01), Martel et al.
patent: 4820817 (1989-04-01), Christensen
patent: 4895939 (1990-01-01), Martel et al.
patent: 5011832 (1991-04-01), Dininno et al.
Shibata, Tet. Letters 26, 4739 (1985).
Sowm, et al, "Enantioselective Synthesis of the 1.beta.-Methylcarbapenems via Cycloaddition of 3-Siloxypentadiene and 4-Acetoxyazetidinone", J.A.C.S., 53, 4154 (1988).
Guthikonda et al, "Structure-Activity Relationships in the 2-Arylcarbapenem Series: Synthesis of 1-Methyl-2-arylcarbapenems", J. Med. Chem., 30, 871 (1987).
Kim et al, "Stereoselective Synthesis of 1-.beta.-Methylcarbapenem", Tetrahedron Letters, 28, 507-510 (1987).

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