HIGHLY ASYMMETRIC PUMMERER-TYPE CYCLIZATION OF CHIRAL, NON-RACEMIC BETA-AMIDO SULFOXIDES
The first highly asymmetric Pummerer-type cyclization of chiral non-racemic beta-amido sulfoxides to enantiomerically enriched beta-lactams (80-85% ee) is described. S- and R-Sulfoxides (S-2a-d and R-2a-c) were treated with O-methyl-O-tert-butyldimethylsilyl ketene acetal 1 in the presence of a cata...
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| Published in | J. Chem. Soc., Perkin Trans. 1 no. 19; pp. 2405 - 2410 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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CAMBRIDGE
Royal Soc Chemistry
1995
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| Abstract | The first highly asymmetric Pummerer-type cyclization of chiral non-racemic beta-amido sulfoxides to enantiomerically enriched beta-lactams (80-85% ee) is described. S- and R-Sulfoxides (S-2a-d and R-2a-c) were treated with O-methyl-O-tert-butyldimethylsilyl ketene acetal 1 in the presence of a catalytic amount of zinc chloride in methylene dichloride to give predominantly the corresponding 4R- and 4S-beta-lactams (R-3a-d and S-3a-c) in more than 80% ee. These results show that the stereoinduction is governed by the absolute configuration of the sulfoxides. Optically pure R- and S-3c were readily obtained by simple recrystallization in about 60% yield, The usefulness of the chiral, non-racemic 4-tolylsulfanyl-beta-lactams 3a-d has been shown by their conversion into the key intermediate 11 for the optically pure carbapenem antibiotic, (+)-PS-5. |
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| AbstractList | The first highly asymmetric Pummerer-type cyclization of chiral non-racemic beta-amido sulfoxides to enantiomerically enriched beta-lactams (80-85% ee) is described. S- and R-Sulfoxides (S-2a-d and R-2a-c) were treated with O-methyl-O-tert-butyldimethylsilyl ketene acetal 1 in the presence of a catalytic amount of zinc chloride in methylene dichloride to give predominantly the corresponding 4R- and 4S-beta-lactams (R-3a-d and S-3a-c) in more than 80% ee. These results show that the stereoinduction is governed by the absolute configuration of the sulfoxides. Optically pure R- and S-3c were readily obtained by simple recrystallization in about 60% yield, The usefulness of the chiral, non-racemic 4-tolylsulfanyl-beta-lactams 3a-d has been shown by their conversion into the key intermediate 11 for the optically pure carbapenem antibiotic, (+)-PS-5. |
| Author | SHIBATA, N FUJITA, S FUJIMORI, C KAWANO, N MATSUMOTO, K KITA, Y TOHJO, T |
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| CitedBy_id | crossref_primary_10_1002_ejoc_201100426 crossref_primary_10_1016_j_tet_2005_10_040 crossref_primary_10_1021_jo0485076 crossref_primary_10_1016_j_tet_2004_09_113 crossref_primary_10_1021_cr020090l crossref_primary_10_1039_C4OB00567H crossref_primary_10_1002_chem_201400117 |
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| Keywords | BIOMIMETIC SYNTHESIS ENANTIOSELECTIVE SYNTHESIS SILYLATED KETENE ACETALS EFFICIENT SYNTHESIS CHEMISTRY CARBAPENEM ANTIBIOTICS 2-(ALKYLTHIO)PENEM-3-CARBOXYLIC ACIDS ACETIC-ANHYDRIDE STEREOSELECTIVE SYNTHESIS LACTAM ANTIBIOTICS |
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| Snippet | The first highly asymmetric Pummerer-type cyclization of chiral non-racemic beta-amido sulfoxides to enantiomerically enriched beta-lactams (80-85% ee) is... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | HIGHLY ASYMMETRIC PUMMERER-TYPE CYCLIZATION OF CHIRAL, NON-RACEMIC BETA-AMIDO SULFOXIDES |
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