Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes

Fatima C. Sequeira; Sherry R. Chemler

doi:10.1021/ol301984b

Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes

Fatima C. Sequeira
, Sherry R. Chemler

Chemistry

SUNY Buffalo

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

87 Scopus citations

Abstract

A new copper(II) 2-ethylhexanoate-promoted addition of an alcohol and an amine across an alkene (oxyamination) is reported. The alcohol addition is intramolecular, while coupling with the amine occurs intermolecularly. Several 2-aminomethyl morpholines were synthesized in good to excellent yields and diastereoselectivities.

Original language	English
Pages (from-to)	4482-4485
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	17
DOIs	https://doi.org/10.1021/ol301984b
State	Published - Sep 7 2012

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10.1021/ol301984b

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title = "Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes",

abstract = "A new copper(II) 2-ethylhexanoate-promoted addition of an alcohol and an amine across an alkene (oxyamination) is reported. The alcohol addition is intramolecular, while coupling with the amine occurs intermolecularly. Several 2-aminomethyl morpholines were synthesized in good to excellent yields and diastereoselectivities.",

author = "Sequeira, \{Fatima C.\} and Chemler, \{Sherry R.\}",

year = "2012",

month = sep,

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doi = "10.1021/ol301984b",

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journal = "Organic Letters",

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T1 - Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes

AU - Sequeira, Fatima C.

AU - Chemler, Sherry R.

PY - 2012/9/7

Y1 - 2012/9/7

N2 - A new copper(II) 2-ethylhexanoate-promoted addition of an alcohol and an amine across an alkene (oxyamination) is reported. The alcohol addition is intramolecular, while coupling with the amine occurs intermolecularly. Several 2-aminomethyl morpholines were synthesized in good to excellent yields and diastereoselectivities.

AB - A new copper(II) 2-ethylhexanoate-promoted addition of an alcohol and an amine across an alkene (oxyamination) is reported. The alcohol addition is intramolecular, while coupling with the amine occurs intermolecularly. Several 2-aminomethyl morpholines were synthesized in good to excellent yields and diastereoselectivities.

UR - https://www.scopus.com/pages/publications/84866053373

U2 - 10.1021/ol301984b

DO - 10.1021/ol301984b

M3 - Article

C2 - 22894680

AN - SCOPUS:84866053373

SN - 1523-7060

VL - 14

SP - 4482

EP - 4485

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes

Abstract

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