Sequential nitromethane conjugate addition/elimination - Pd-catalyzed allylation of β-trifloxy acrylates. Application to carbapenem synthesis

John Y.L. Chung; Edward J.J. Grabowski; Paul J. Reider

doi:10.1021/ol990299u

Sequential nitromethane conjugate addition/elimination - Pd-catalyzed allylation of β-trifloxy acrylates. Application to carbapenem synthesis

John Y.L. Chung, Edward J.J. Grabowski, Paul J. Reider

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

10 Scopus citations

Abstract

(formula presented) Sequential reactions of nitromethane via conjugate addition - elimination to B-trifloxy acrylates followed by Pd-catalyzed substitution of the resulting allyl nitro compounds with nucleophiles afforded homologation products at the β-position. 2-Naphthosultammethyl carbapenem, pan anti-MRS carbapenem intermediate, was prepared in one pot from the corresponding 2-trifloxy compound. The scope and limitation of the one-pot method were investigated using several cyclic unsaturated esters and nucleophiles.

Original language	English (US)
Pages (from-to)	1783-1785
Number of pages	3
Journal	Organic letters
Volume	1
Issue number	11
DOIs	https://doi.org/10.1021/ol990299u
State	Published - Dec 2 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol990299u

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title = "Sequential nitromethane conjugate addition/elimination - Pd-catalyzed allylation of β-trifloxy acrylates. Application to carbapenem synthesis",

abstract = "(formula presented) Sequential reactions of nitromethane via conjugate addition - elimination to B-trifloxy acrylates followed by Pd-catalyzed substitution of the resulting allyl nitro compounds with nucleophiles afforded homologation products at the β-position. 2-Naphthosultammethyl carbapenem, pan anti-MRS carbapenem intermediate, was prepared in one pot from the corresponding 2-trifloxy compound. The scope and limitation of the one-pot method were investigated using several cyclic unsaturated esters and nucleophiles.",

author = "Chung, \{John Y.L.\} and Grabowski, \{Edward J.J.\} and Reider, \{Paul J.\}",

year = "1999",

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doi = "10.1021/ol990299u",

language = "English (US)",

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journal = "Organic letters",

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T1 - Sequential nitromethane conjugate addition/elimination - Pd-catalyzed allylation of β-trifloxy acrylates. Application to carbapenem synthesis

AU - Chung, John Y.L.

AU - Grabowski, Edward J.J.

AU - Reider, Paul J.

PY - 1999/12/2

Y1 - 1999/12/2

N2 - (formula presented) Sequential reactions of nitromethane via conjugate addition - elimination to B-trifloxy acrylates followed by Pd-catalyzed substitution of the resulting allyl nitro compounds with nucleophiles afforded homologation products at the β-position. 2-Naphthosultammethyl carbapenem, pan anti-MRS carbapenem intermediate, was prepared in one pot from the corresponding 2-trifloxy compound. The scope and limitation of the one-pot method were investigated using several cyclic unsaturated esters and nucleophiles.

AB - (formula presented) Sequential reactions of nitromethane via conjugate addition - elimination to B-trifloxy acrylates followed by Pd-catalyzed substitution of the resulting allyl nitro compounds with nucleophiles afforded homologation products at the β-position. 2-Naphthosultammethyl carbapenem, pan anti-MRS carbapenem intermediate, was prepared in one pot from the corresponding 2-trifloxy compound. The scope and limitation of the one-pot method were investigated using several cyclic unsaturated esters and nucleophiles.

UR - https://www.scopus.com/pages/publications/0001406203

UR - https://www.scopus.com/inward/citedby.url?scp=0001406203&partnerID=8YFLogxK

U2 - 10.1021/ol990299u

DO - 10.1021/ol990299u

M3 - Article

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SN - 1523-7060

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SP - 1783

EP - 1785

JO - Organic letters

JF - Organic letters

IS - 11

ER -

Sequential nitromethane conjugate addition/elimination - Pd-catalyzed allylation of β-trifloxy acrylates. Application to carbapenem synthesis

Abstract

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