New chiral phosphinephosphinite ligands: Application to stereoselective synthesis of a key intermediate of 1{beta}-methyl carbapenems by Rh(I)-catalyzed asymmetric hydroformylation

Conference · Sun Dec 31 04:00:00 EST 1995

OSTI ID:250106

Saito, Takao; Yoshida, Akifumi; Matsumura, Kazuhiko ^[1]

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1. Takasago International Corp., Kanagawa (Japan); and others

Transition metal catalyzed asymmetric hydroformylation is an attractive and highly useful homologation process for organic synthesis. Recently, the authors reported that the Rh(I) complexes of phosphinephosphite BINAPHOS are highly efficient catalysts for enantioselective hydroformylation of a variety of olefins. This time, the authors have designed and synthesized new chiral phosphinephosphinite ligands having binaphthyl backbone, (R)-2-diarylphosphino-2{prime}-diarylphosphinoxy-1,1{prime}-binaphthy1 (hereafter abbreviated (R)-BIPNITE). The Rh(I) complexes of these ligands are effective catalysts for the asymmetric hydroformylation of 4-vinylazetidin-2-one to give the corresponding oxo-aldehyde 3{beta} as the major product in very high diastereoselectivities and in good regioselectivities. Interestingly, modifications of the aryl substituents in phosphine and phosphinite moieties afforded higher selectivities. Aldehyde 3{beta} was easily oxidized with NaClO{sub 2} to 4, a key intermediate of 1{beta}-methyl carbapenems. Thus, the present method provides a new practical route to a versatile key intermediate for the synthesis of carbapenem antibiotics.

• OSTI ID: 250106
• Report Number(s): CONF-9508100--
• Country of Publication: United States
• Language: English

Related Subjects

40 CHEMISTRY
ALKENES
CARBONYLATION
CATALYTIC EFFECTS
CHEMICAL PREPARATION
LIGANDS
ORGANIC COMPOUNDS
ORGANOMETALLIC COMPOUNDS
REACTION INTERMEDIATES
RHODIUM COMPLEXES
STEREOCHEMISTRY