Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes

Wei Zeng; Sherry R. Chemler

doi:10.1021/ja0762240

Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes

Wei Zeng
, Sherry R. Chemler

Chemistry

SUNY Buffalo

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

245 Scopus citations

Abstract

The enantioselective oxidative cyclizations of γ-alkenyl arylsulfonamides and a δ-alkenyl arylsulfonamide for the synthesis of nitrogen heterocycles are presented. The reactions are catalyzed by chiral copper(II) complexes, and MnO₂ is used as the inexpensive stoichiometric oxidant. A variety of five-membered heterocycles and a tetrahydroisoquinoline have been synthesized in good to excellent yields with good to excellent levels of enantioselectivity. This is the first reported copper-catalyzed enantioselective carboamination of alkenes.

Original language	English
Pages (from-to)	12948-12949
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	43
DOIs	https://doi.org/10.1021/ja0762240
State	Published - Oct 31 2007

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abstract = "The enantioselective oxidative cyclizations of γ-alkenyl arylsulfonamides and a δ-alkenyl arylsulfonamide for the synthesis of nitrogen heterocycles are presented. The reactions are catalyzed by chiral copper(II) complexes, and MnO2 is used as the inexpensive stoichiometric oxidant. A variety of five-membered heterocycles and a tetrahydroisoquinoline have been synthesized in good to excellent yields with good to excellent levels of enantioselectivity. This is the first reported copper-catalyzed enantioselective carboamination of alkenes.",

author = "Wei Zeng and Chemler, \{Sherry R.\}",

year = "2007",

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T1 - Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes

AU - Zeng, Wei

AU - Chemler, Sherry R.

PY - 2007/10/31

Y1 - 2007/10/31

N2 - The enantioselective oxidative cyclizations of γ-alkenyl arylsulfonamides and a δ-alkenyl arylsulfonamide for the synthesis of nitrogen heterocycles are presented. The reactions are catalyzed by chiral copper(II) complexes, and MnO2 is used as the inexpensive stoichiometric oxidant. A variety of five-membered heterocycles and a tetrahydroisoquinoline have been synthesized in good to excellent yields with good to excellent levels of enantioselectivity. This is the first reported copper-catalyzed enantioselective carboamination of alkenes.

AB - The enantioselective oxidative cyclizations of γ-alkenyl arylsulfonamides and a δ-alkenyl arylsulfonamide for the synthesis of nitrogen heterocycles are presented. The reactions are catalyzed by chiral copper(II) complexes, and MnO2 is used as the inexpensive stoichiometric oxidant. A variety of five-membered heterocycles and a tetrahydroisoquinoline have been synthesized in good to excellent yields with good to excellent levels of enantioselectivity. This is the first reported copper-catalyzed enantioselective carboamination of alkenes.

UR - https://www.scopus.com/pages/publications/35848934578

U2 - 10.1021/ja0762240

DO - 10.1021/ja0762240

M3 - Article

C2 - 17918850

AN - SCOPUS:35848934578

SN - 0002-7863

VL - 129

SP - 12948

EP - 12949

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 43

ER -

Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes

Abstract

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