Enantio- and Diastereoselective Synthesis of Homopropargyl Amines by Copper-Catalyzed Coupling of Imines, 1,3-Enynes, and Diborons

Srimanta Manna; Quentin Dherbassy; Gregory J. P. Perry; David John Procter

doi:10.1002/anie.201915191

Enantio- and Diastereoselective Synthesis of Homopropargyl Amines by Copper-Catalyzed Coupling of Imines, 1,3-Enynes, and Diborons

Srimanta Manna, Quentin Dherbassy, Gregory J. P. Perry, David John Procter

Organic Chemistry Group

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Abstract

An efficient, enantio‐ and diastereoselective, copper‐catalyzed coupling of imines, 1,3‐enynes, and diborons is reported. The process shows broad substrate scope and delivers complex, chiral homopropargyl amines; useful building blocks en route to biologically‐relevant compounds. In particular, functionalized homopropargyl amines bearing up to three contiguous stereocenters can be prepared in a single step.

Original language	English
Journal	Angewandte Chemie International Edition
Early online date	9 Jan 2020
DOIs	https://doi.org/10.1002/anie.201915191
Publication status	Published - 2020

Keywords

copper
borylative coupling
homopropargyl amines
1, 3-enynes
asymmetric catalysis

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DJP-SM-QD-manuscript-Angew-Jan9Accepted author manuscript, 815 KB

http://doi.wiley.com/10.1002/anie.201915191

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title = "Enantio- and Diastereoselective Synthesis of Homopropargyl Amines by Copper-Catalyzed Coupling of Imines, 1,3-Enynes, and Diborons",

abstract = "An efficient, enantio‐ and diastereoselective, copper‐catalyzed coupling of imines, 1,3‐enynes, and diborons is reported. The process shows broad substrate scope and delivers complex, chiral homopropargyl amines; useful building blocks en route to biologically‐relevant compounds. In particular, functionalized homopropargyl amines bearing up to three contiguous stereocenters can be prepared in a single step.",

keywords = "copper, borylative coupling, homopropargyl amines, 1, 3-enynes, asymmetric catalysis",

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doi = "10.1002/anie.201915191",

language = "English",

journal = "Angewandte Chemie International Edition",

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T1 - Enantio- and Diastereoselective Synthesis of Homopropargyl Amines by Copper-Catalyzed Coupling of Imines, 1,3-Enynes, and Diborons

AU - Manna, Srimanta

AU - Dherbassy, Quentin

AU - Perry, Gregory J. P.

AU - Procter, David John

PY - 2020

Y1 - 2020

N2 - An efficient, enantio‐ and diastereoselective, copper‐catalyzed coupling of imines, 1,3‐enynes, and diborons is reported. The process shows broad substrate scope and delivers complex, chiral homopropargyl amines; useful building blocks en route to biologically‐relevant compounds. In particular, functionalized homopropargyl amines bearing up to three contiguous stereocenters can be prepared in a single step.

AB - An efficient, enantio‐ and diastereoselective, copper‐catalyzed coupling of imines, 1,3‐enynes, and diborons is reported. The process shows broad substrate scope and delivers complex, chiral homopropargyl amines; useful building blocks en route to biologically‐relevant compounds. In particular, functionalized homopropargyl amines bearing up to three contiguous stereocenters can be prepared in a single step.

KW - copper

KW - borylative coupling

KW - homopropargyl amines

KW - 1, 3-enynes

KW - asymmetric catalysis

U2 - 10.1002/anie.201915191

DO - 10.1002/anie.201915191

M3 - Article

SN - 1433-7851

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

ER -

Enantio- and Diastereoselective Synthesis of Homopropargyl Amines by Copper-Catalyzed Coupling of Imines, 1,3-Enynes, and Diborons

Abstract

Keywords

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