A Facially-Selective Protonation Controls the Stereochemistry of a Key Intermediate in the Synthesis of 1β-Methylcarbapenems

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

doi:10.1021/jo00093a001

A Facially-Selective Protonation Controls the Stereochemistry of a Key Intermediate in the Synthesis of 1β-Methylcarbapenems

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

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

12 Scopus citations

Abstract

Investigation into the selectivity observed in the synthesis of 1β-methylcarbapenems was carried out by examining (1) the rotational barrier between the two possible ketene acetal conformations A and B and (2) the protonation of ketene acetal 3 to the mono acid product 2, using the MNDO Hamiltonian.

Original language	English (US)
Pages (from-to)	3749-3751
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	59
Issue number	14
DOIs	https://doi.org/10.1021/jo00093a001
State	Published - Jul 1 1994
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00093a001

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title = "A Facially-Selective Protonation Controls the Stereochemistry of a Key Intermediate in the Synthesis of 1β-Methylcarbapenems",

abstract = "Investigation into the selectivity observed in the synthesis of 1β-methylcarbapenems was carried out by examining (1) the rotational barrier between the two possible ketene acetal conformations A and B and (2) the protonation of ketene acetal 3 to the mono acid product 2, using the MNDO Hamiltonian.",

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

year = "1994",

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day = "1",

doi = "10.1021/jo00093a001",

language = "English (US)",

volume = "59",

pages = "3749--3751",

journal = "Journal of Organic Chemistry",

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publisher = "American Chemical Society",

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T1 - A Facially-Selective Protonation Controls the Stereochemistry of a Key Intermediate in the Synthesis of 1β-Methylcarbapenems

AU - Jones, Deborah K.

AU - Liotta, Dennis C.

AU - Choi, Woo Baeg

AU - Volante, R. P.

AU - Reider, Paul J.

AU - Shinkai, Ichiro

AU - Churchill, Hywyn R.O.

AU - Lynch, Joseph E.

PY - 1994/7/1

Y1 - 1994/7/1

N2 - Investigation into the selectivity observed in the synthesis of 1β-methylcarbapenems was carried out by examining (1) the rotational barrier between the two possible ketene acetal conformations A and B and (2) the protonation of ketene acetal 3 to the mono acid product 2, using the MNDO Hamiltonian.

AB - Investigation into the selectivity observed in the synthesis of 1β-methylcarbapenems was carried out by examining (1) the rotational barrier between the two possible ketene acetal conformations A and B and (2) the protonation of ketene acetal 3 to the mono acid product 2, using the MNDO Hamiltonian.

UR - https://www.scopus.com/pages/publications/0027941121

UR - https://www.scopus.com/pages/publications/0027941121#tab=citedBy

U2 - 10.1021/jo00093a001

DO - 10.1021/jo00093a001

M3 - Article

AN - SCOPUS:0027941121

SN - 0022-3263

VL - 59

SP - 3749

EP - 3751

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 14

ER -

A Facially-Selective Protonation Controls the Stereochemistry of a Key Intermediate in the Synthesis of 1β-Methylcarbapenems

Abstract

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