1,3-Dipolar cycloadditions of 2-tert-butoxycarbonyl-1-pyrroline N-oxide with chiral acrylates and acrylamides

Federica Pisaneschi; Martina Gensini; Maria Salvati; Franca M. Cordero; Alberto Brandi

doi:10.3987/COM-05-S(T)37

1,3-Dipolar cycloadditions of 2-tert-butoxycarbonyl-1-pyrroline N-oxide with chiral acrylates and acrylamides

Federica Pisaneschi, Martina Gensini, Maria Salvati, Franca M. Cordero, Alberto Brandi

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

11 Scopus citations

Abstract

The 1,3-dipolar cycloadditions of a series of chiral acrylates and acrylamides with 2-tert-butoxycarbonyl-1-pyrroline N-oxide were studied. The synthesis of enantiopure tert-butyl (2R,7aR)- and (2S,7aS)-2-hydroxy-3-oxo-tetrahydro-1H-pyrrolizine-7a(5H)-carboxylates starting from the acryloyloxazolidinone derived from (S)-phenylalanine is reported.

Original language	English (US)
Pages (from-to)	413-420
Number of pages	8
Journal	Heterocycles
Volume	67
Issue number	1
DOIs	https://doi.org/10.3987/COM-05-S(T)37
State	Published - Jan 1 2006
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "The 1,3-dipolar cycloadditions of a series of chiral acrylates and acrylamides with 2-tert-butoxycarbonyl-1-pyrroline N-oxide were studied. The synthesis of enantiopure tert-butyl (2R,7aR)- and (2S,7aS)-2-hydroxy-3-oxo-tetrahydro-1H-pyrrolizine-7a(5H)-carboxylates starting from the acryloyloxazolidinone derived from (S)-phenylalanine is reported.",

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doi = "10.3987/COM-05-S(T)37",

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T1 - 1,3-Dipolar cycloadditions of 2-tert-butoxycarbonyl-1-pyrroline N-oxide with chiral acrylates and acrylamides

AU - Pisaneschi, Federica

AU - Gensini, Martina

AU - Salvati, Maria

AU - Cordero, Franca M.

AU - Brandi, Alberto

PY - 2006/1/1

Y1 - 2006/1/1

N2 - The 1,3-dipolar cycloadditions of a series of chiral acrylates and acrylamides with 2-tert-butoxycarbonyl-1-pyrroline N-oxide were studied. The synthesis of enantiopure tert-butyl (2R,7aR)- and (2S,7aS)-2-hydroxy-3-oxo-tetrahydro-1H-pyrrolizine-7a(5H)-carboxylates starting from the acryloyloxazolidinone derived from (S)-phenylalanine is reported.

AB - The 1,3-dipolar cycloadditions of a series of chiral acrylates and acrylamides with 2-tert-butoxycarbonyl-1-pyrroline N-oxide were studied. The synthesis of enantiopure tert-butyl (2R,7aR)- and (2S,7aS)-2-hydroxy-3-oxo-tetrahydro-1H-pyrrolizine-7a(5H)-carboxylates starting from the acryloyloxazolidinone derived from (S)-phenylalanine is reported.

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1,3-Dipolar cycloadditions of 2-tert-butoxycarbonyl-1-pyrroline N-oxide with chiral acrylates and acrylamides

Abstract

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