Diastereoselective synthesis of a key intermediate for the preparation of tricyclic β-lactam antibiotics

Tetrahedron Letters

Volumn 40, Issue 27, 1999, Pages 5043-5046

  Matsumoto, Takaji ^a   Murayama, Toshiyuki ^a   Mitsuhashi, Shigeru ^a   Miura, Takashi ^a  

^a TAKASAGO INTERNATIONAL CORPORATION   (Japan)

Author keywords

Aldol reactions; Asymmetric synthesis; Carbapenems; Hydrogenation

Indexed keywords

SANFETRINEM;

ARTICLE; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; OXIDATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0033516545     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00929-6     Document Type: Article

References (13)

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8. BINAP=2,2'-bis(diphenylphosphino)-1,1'-binaphthyl. (Formula Presented)
9. Ohkuma T, Ooka H, Yamakawa M, Ikariya T, Noyori R. J. Org. Chem. 1996;61:4872.
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11. 3 gave (S)-5 with 99%ee. The absolute configuration of 5 was determined by sign of optical rotation to be (S)-form; see ref [3a]. The enantiomeric excess was determined by GC analysis using Chiraldex G-TA.
12. Andreotti D, Rossi T, Gaviraghi G, Donati D, Marchioro C, Di Modugno E, Perboni A. Bioorg. Med. Chem. Lett. 1996;6:491.
13. 4. Removal of the solvent gave a crude product as an oil (w/w assay by HPLC 85%).