3-hydroxy gamma-lactone based enantioselective synthesis of azet

Details 3-hydroxy gamma-lactone based enantioselective synthesis of azet 3-hydroxy gamma-lactone based enantioselective synthesis of azet

1997-05-28

1999-03-23

Berch, Mark L

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20508

Patent

active

058861718

ABSTRACT:
The invention relates to a process for producing a compound of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined in the specification, which comprises the steps of: (a) reacting a lactone with an imine to obtain a chiral diol of the formula IV; (b) oxidizing the diol to obtain an aldehyde of formula V; (c) condensing the aldehyde with an enolether followed by dehydration to obtain a compound of formula VI; (d) hydrogenating the compound of formula VI to obtain a ketone of formula VII; and (e) chirally catalytically reducing the ketone, wherein steps (b)-(d) are shown in the following reaction scheme: ##STR2##

REFERENCES:
patent: 5292939 (1994-03-01), Hollingsworth
patent: 5739321 (1998-04-01), Wu
O'Leary, J. Chem Research (S) 368, Aug. 1996.
Panfil et al, Tetrahedron, vol. 47, No. 48 (1991), pp. 10087-10094.
Panfil et al, Chemical Abstracts, vol. 109, 38139j. (1987).

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