Anchimeric Assistance in the Case of Vicinal Dimesylate: Formation of Enantiomeric or meso-Bimorpholine

Tõnis Kanger; Marju Laars; Kadri Kriis; Tiiu Kailas; Aleksander-Mati Müürisepp; Tõnis Pehk; Margus Lopp

doi:10.1055/s-2006-926469

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Anchimeric Assistance in the Case of Vicinal Dimesylate: Formation of Enantiomeric or meso-Bimorpholine

Tõnis Kanger*^a, Marju Laars^a, Kadri Kriis^a, Tiiu Kailas^a, Aleksander-Mati Müürisepp^a, Tõnis Pehk^b, Margus Lopp^a
^a Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia
^b National Institute of Chemical Physics and Biophysics, Akadeemia tee 23, 12618 Tallinn, Estonia
Fax: +372(6)202828; e-Mail: kanger@chemnet.ee;

Abstract

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Abstract

An anchimeric effect of vicinal dimesylate in the intramolecular nucleophilic substitution by amine is described. One sulfonate group of the dimesylate acts as an internal nucleophile and the other as a leaving group, affording meso-bimorpholine in the intramolecular cyclization. ω,ω′-Dimesylate omits this effect and the target compound is obtained with high ee.

Key words

neighboring-group effects - cyclizations - asymmetric synthesis - amines - stereoselectivity

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Referenzen

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