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Synthesis of β-Allenylamines by Addition of Chloroprene Grignards to N-Boc Imines

Arne G. A. Geissler and Bernhard Breit*

*Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, Freiburg 79104, Germany, Email: bernhard.breitchemie.uni-freiburg.de

A. G. A. Geissler, B. Breit, Org. Lett., 2022, 24, 7967-7971.

DOI: 10.1021/acs.orglett.2c03105


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Abstract

2,2'-Dimorpholinodiethyl ether (DMDEE) mediates a γ-selective addition of chloroprene Grignards to aromatic N-Boc aldimines to provide the corresponding N-Boc protected β-allenylamines in good yields and regioselectivities. Transmetalation to zinc bromide also allows the addition of chloroprene Grignard to aliphatic aldimines in good yields.

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Addition of Chloroprene Grignards to Aromatic Aldehydes: Synthesis of Homoallenyl Alcohols

A. G. A. Geissler, B. Breit, Org. Lett., 2021, 23, 2621-2625.


Key Words

homoallylic amines, allenes


ID: J54-Y2022