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2005
Hydrogenated naphthalene derivatives
Q 1010
Copper-Catalyzed anti-Stereocontrolled Ring-Opening of Azabicyclic Alkenes
Grignard Reagents. — The combination of a (2-pyridyl)sulfonyl moiety as an
21- 107 with
activating group at the nitrogen, CuCN (or CuCl) as a catalyst, and Grignard reagents
as nucleophiles results in a novel and efficient anti-stereocontrolled copper-catalyzed
protocol for the ring-opening reaction of azabicyclic alkenes. The reaction proceeds
with good yields and excellent stereoselectivity (generally ≥96% d.e.) affording dihydronaphthalene-1-amines as scaffolds for bioactive substances. Furthermore, an effective way of deprotection is described. — (GOMEZ ARRAYAS*, R.; CABRERA, S.;
CARRETERO, J. C.; Org. Lett. 7 (2005) 2, 219-221; Dep. Quim. Org., Fac. Cienc.,
Univ. Auton., Cantoblanco, E-28049 Madrid, Spain; Eng.) — Steudel
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