An unusual stereoselective decarboxylation: A key reaction to an important intermediate for carbapenem antibiotics

被引:5
作者
Choi, WB [1 ]
Churchill, HRO [1 ]
Lynch, JE [1 ]
Volante, RP [1 ]
Reider, PJ [1 ]
Shinkai, I [1 ]
Jones, DK [1 ]
Liotta, DC [1 ]
机构
[1] EMORY UNIV,DEPT CHEM,ATLANTA,GA 30322
关键词
D O I
10.1021/jo00131a010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The dramatic difference in reactivity of the two diastereomeric acid esters 4A and 4B during decarboxylation has been thoroughly investigated, The (R) isomer 4A underwent decarboxylation to provide a 94:6 mixture of 5A and 5B at 80 degrees C in 5-6 h. Under the same conditions the (S) isomer 4B did not undergo decarboxylation and with further heating to 120 degrees C gave mainly the ring-opened decomposition product 6 along with unidentified decomposition products, A mechanistic rationale for this unusual reactivity profile is provided.
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页码:8367 / 8370
页数:4
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