Copper(II) carboxylate promoted intramolecular diamination of terminal alkenes: Improved reaction conditions and expanded substrate scope

Thomas P. Zabawa; Sherry R. Chemler

doi:10.1021/ol0706713

Copper(II) carboxylate promoted intramolecular diamination of terminal alkenes: Improved reaction conditions and expanded substrate scope

Thomas P. Zabawa
, Sherry R. Chemler

Chemistry

SUNY Buffalo

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

105 Scopus citations

Abstract

The copper(II) carboxylate promoted diamination reaction has been improved by the use of the organic soluble copper(II) neodecanoate [Cu(ND)₂]. Cu(ND)₂ allowed the less-polar solvent dichloroethane (DCE) to be used, and as a consequence, decomposition of less-reactive substrates could be avoided. High diastereoselectivity was observed in the synthesis of 2,5-disubstituted pyrrolidines. Ureas, bis(anllines), and α-amido pyrroles derived from 2-allylaniline could also participate in the diamination reaction.

Original language	English
Pages (from-to)	2035-2038
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	10
DOIs	https://doi.org/10.1021/ol0706713
State	Published - May 10 2007

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title = "Copper(II) carboxylate promoted intramolecular diamination of terminal alkenes: Improved reaction conditions and expanded substrate scope",

abstract = "The copper(II) carboxylate promoted diamination reaction has been improved by the use of the organic soluble copper(II) neodecanoate [Cu(ND)2]. Cu(ND)2 allowed the less-polar solvent dichloroethane (DCE) to be used, and as a consequence, decomposition of less-reactive substrates could be avoided. High diastereoselectivity was observed in the synthesis of 2,5-disubstituted pyrrolidines. Ureas, bis(anllines), and α-amido pyrroles derived from 2-allylaniline could also participate in the diamination reaction.",

author = "Zabawa, \{Thomas P.\} and Chemler, \{Sherry R.\}",

year = "2007",

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doi = "10.1021/ol0706713",

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journal = "Organic Letters",

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T1 - Copper(II) carboxylate promoted intramolecular diamination of terminal alkenes

T2 - Improved reaction conditions and expanded substrate scope

AU - Zabawa, Thomas P.

AU - Chemler, Sherry R.

PY - 2007/5/10

Y1 - 2007/5/10

N2 - The copper(II) carboxylate promoted diamination reaction has been improved by the use of the organic soluble copper(II) neodecanoate [Cu(ND)2]. Cu(ND)2 allowed the less-polar solvent dichloroethane (DCE) to be used, and as a consequence, decomposition of less-reactive substrates could be avoided. High diastereoselectivity was observed in the synthesis of 2,5-disubstituted pyrrolidines. Ureas, bis(anllines), and α-amido pyrroles derived from 2-allylaniline could also participate in the diamination reaction.

AB - The copper(II) carboxylate promoted diamination reaction has been improved by the use of the organic soluble copper(II) neodecanoate [Cu(ND)2]. Cu(ND)2 allowed the less-polar solvent dichloroethane (DCE) to be used, and as a consequence, decomposition of less-reactive substrates could be avoided. High diastereoselectivity was observed in the synthesis of 2,5-disubstituted pyrrolidines. Ureas, bis(anllines), and α-amido pyrroles derived from 2-allylaniline could also participate in the diamination reaction.

UR - https://www.scopus.com/pages/publications/34249306530

U2 - 10.1021/ol0706713

DO - 10.1021/ol0706713

M3 - Article

C2 - 17447781

AN - SCOPUS:34249306530

SN - 1523-7060

VL - 9

SP - 2035

EP - 2038

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Copper(II) carboxylate promoted intramolecular diamination of terminal alkenes: Improved reaction conditions and expanded substrate scope

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