Preparation of enantioselective enriched α-(dialkoxyphosphoryl) lactams via intramolecular C-H insertion with chiral dirhodium(II) catalysts

Pedro M. Pedro; Nuno R. Candeias; Carlos A.M. Afonso

doi:10.1016/j.molcata.2004.09.041

Preparation of enantioselective enriched α-(dialkoxyphosphoryl) lactams via intramolecular C-H insertion with chiral dirhodium(II) catalysts

Pedro M. Pedro, Nuno R. Candeias, Carlos A.M. Afonso

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29 Citations (Scopus)

Abstract

The intramolecular C-H insertion on alpha-diazoacetamides is an extremely useful procedure for the preparation of a wide variety of heterocyclic compounds. In this work is presented a strategy for the preparation of enantioselective enriched alpha-(dialkoxyphosphoryl)lactams via dirhodium(II) catalyzed C-H insertion on alpha-diazo-alpha-(dialkoxyphosphoryl)acetamides, in which enantiomeric excess up to 40% is reported. Moreover, a systematic study was undertaken on the chiral dirhodium(II) catalyst and the alpha-diazo-alpha-(dialkoxyphosphoryl)acetamides influence on enantioselectivity. (C) 2004 Elsevier B.V. All rights reserved.

Original language	English
Pages (from-to)	17-24
Number of pages	8
Journal	Journal Of Molecular Catalysis A-Chemical
Volume	227
Issue number	1-2
DOIs	https://doi.org/10.1016/j.molcata.2004.09.041 https://doi.org/10.1016/j.molcata.2004.09.041
Publication status	Published - 1 Mar 2005

Keywords

Phosphonates
Rhodium catalysts
CH insertion
Diazo compounds
Lactams

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title = "Preparation of enantioselective enriched α-(dialkoxyphosphoryl) lactams via intramolecular C-H insertion with chiral dirhodium(II) catalysts",

abstract = "The intramolecular C-H insertion on alpha-diazoacetamides is an extremely useful procedure for the preparation of a wide variety of heterocyclic compounds. In this work is presented a strategy for the preparation of enantioselective enriched alpha-(dialkoxyphosphoryl)lactams via dirhodium(II) catalyzed C-H insertion on alpha-diazo-alpha-(dialkoxyphosphoryl)acetamides, in which enantiomeric excess up to 40% is reported. Moreover, a systematic study was undertaken on the chiral dirhodium(II) catalyst and the alpha-diazo-alpha-(dialkoxyphosphoryl)acetamides influence on enantioselectivity. (C) 2004 Elsevier B.V. All rights reserved.",

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T1 - Preparation of enantioselective enriched α-(dialkoxyphosphoryl) lactams via intramolecular C-H insertion with chiral dirhodium(II) catalysts

AU - Pedro, Pedro M.

AU - Candeias, Nuno R.

AU - Afonso, Carlos A.M.

PY - 2005/3/1

Y1 - 2005/3/1

N2 - The intramolecular C-H insertion on alpha-diazoacetamides is an extremely useful procedure for the preparation of a wide variety of heterocyclic compounds. In this work is presented a strategy for the preparation of enantioselective enriched alpha-(dialkoxyphosphoryl)lactams via dirhodium(II) catalyzed C-H insertion on alpha-diazo-alpha-(dialkoxyphosphoryl)acetamides, in which enantiomeric excess up to 40% is reported. Moreover, a systematic study was undertaken on the chiral dirhodium(II) catalyst and the alpha-diazo-alpha-(dialkoxyphosphoryl)acetamides influence on enantioselectivity. (C) 2004 Elsevier B.V. All rights reserved.

AB - The intramolecular C-H insertion on alpha-diazoacetamides is an extremely useful procedure for the preparation of a wide variety of heterocyclic compounds. In this work is presented a strategy for the preparation of enantioselective enriched alpha-(dialkoxyphosphoryl)lactams via dirhodium(II) catalyzed C-H insertion on alpha-diazo-alpha-(dialkoxyphosphoryl)acetamides, in which enantiomeric excess up to 40% is reported. Moreover, a systematic study was undertaken on the chiral dirhodium(II) catalyst and the alpha-diazo-alpha-(dialkoxyphosphoryl)acetamides influence on enantioselectivity. (C) 2004 Elsevier B.V. All rights reserved.

KW - Phosphonates

KW - Rhodium catalysts

KW - CH insertion

KW - Diazo compounds

KW - Lactams

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JO - Journal Of Molecular Catalysis A-Chemical

JF - Journal Of Molecular Catalysis A-Chemical

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Preparation of enantioselective enriched α-(dialkoxyphosphoryl) lactams via intramolecular C-H insertion with chiral dirhodium(II) catalysts

Abstract

Keywords

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