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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 26期

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.

引用

页码：8367 / 8370

页数：4

共 14 条

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