An Unusual Stereoselective Decarboxylation: A Key Reaction to an Important Intermediate for Carbapenem Antibiotics

Woo Baeg Choi; Hywyn R.O. Churchill; Joseph E. Lynch; R. P. Volante; Paul J. Reider; Ichiro Shinkai; Deborah K. Jones; Dennis C. Liotta

doi:10.1021/jo00131a010

An Unusual Stereoselective Decarboxylation: A Key Reaction to an Important Intermediate for Carbapenem Antibiotics

Woo Baeg Choi, Hywyn R.O. Churchill, Joseph E. Lynch, R. P. Volante, Paul J. Reider, Ichiro Shinkai, Deborah K. Jones, Dennis C. Liotta

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

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 °C in 5-6 h. Under the same conditions the (S) isomer 4B did not undergo decarboxylation and with further heating to 120 °C gave mainly the ring-opened decomposition product 6 along with unidentified decomposition products. A mechanistic rationale for this unusual reactivity profile is provided.

Original language	English (US)
Pages (from-to)	8367-8370
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	60
Issue number	26
DOIs	https://doi.org/10.1021/jo00131a010
State	Published - Dec 1 1995
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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title = "An Unusual Stereoselective Decarboxylation: A Key Reaction to an Important Intermediate for Carbapenem Antibiotics",

abstract = "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 °C in 5-6 h. Under the same conditions the (S) isomer 4B did not undergo decarboxylation and with further heating to 120 °C gave mainly the ring-opened decomposition product 6 along with unidentified decomposition products. A mechanistic rationale for this unusual reactivity profile is provided.",

author = "Choi, {Woo Baeg} and Churchill, {Hywyn R.O.} and Lynch, {Joseph E.} and Volante, {R. P.} and Reider, {Paul J.} and Ichiro Shinkai and Jones, {Deborah K.} and Liotta, {Dennis C.}",

year = "1995",

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doi = "10.1021/jo00131a010",

language = "English (US)",

volume = "60",

pages = "8367--8370",

journal = "Journal of Organic Chemistry",

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TY - JOUR

T1 - An Unusual Stereoselective Decarboxylation

T2 - A Key Reaction to an Important Intermediate for Carbapenem Antibiotics

AU - Choi, Woo Baeg

AU - Churchill, Hywyn R.O.

AU - Lynch, Joseph E.

AU - Volante, R. P.

AU - Reider, Paul J.

AU - Shinkai, Ichiro

AU - Jones, Deborah K.

AU - Liotta, Dennis C.

PY - 1995/12/1

Y1 - 1995/12/1

N2 - 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 °C in 5-6 h. Under the same conditions the (S) isomer 4B did not undergo decarboxylation and with further heating to 120 °C gave mainly the ring-opened decomposition product 6 along with unidentified decomposition products. A mechanistic rationale for this unusual reactivity profile is provided.

AB - 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 °C in 5-6 h. Under the same conditions the (S) isomer 4B did not undergo decarboxylation and with further heating to 120 °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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DO - 10.1021/jo00131a010

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SP - 8367

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 26

ER -

An Unusual Stereoselective Decarboxylation: A Key Reaction to an Important Intermediate for Carbapenem Antibiotics

Abstract

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