A Comparative Study of the Synthesis of C2-Symmetric Chiral 2,2′-Biaziridinyls

Tõnis Kanger; Kerti Ausmees; Aleksander-Mati Müürisepp; Tõnis Pehk; Margus Lopp

doi:10.1055/s-2003-39303

LETTER

A Comparative Study of the Synthesis of C₂-Symmetric Chiral 2,2′-Biaziridinyls

Tõnis Kanger*^a, Kerti Ausmees^a, Aleksander-Mati Müürisepp^a, Tõnis Pehk^b, Margus Lopp^a
^a Department of Chemistry, Tallinn Technical University, Akadeemia tee 15, Tallinn 12618, Estonia
Fax: +3726547520; e-Mail: kanger@chemnet.ee ;
^b National Institute of Chemical Physics and Biophysics, Akadeemia tee 23, Tallinn 12618, Estonia

Abstract

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Abstract

Two comparative synthetic routes to new enantiomeric C₂-symmetric Boc-protected biaziridinyls from tartaric ester were studied. Simplicity, high enantiomeric purity and high chemical yield of the target compound characterize the proposed methods. Also, unprotected biaziridinyl was synthesized and fully characterized.

Key words

stereoselective synthesis - azides - heterocycles - chiral auxiliaries

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References

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General experimental procedure for the Staudinger reaction using polymer-supported PPh₃: To a solution of azidodiol 2 (1.1 mmol) in anhydrous acetonitrile (12 mL) polymer-supported PPh₃ (2% DVB, 3.3 mmol) was added and the solution was stirred for 3 h at room temperature followed by reflux for 11 h. The resin was filtered, the filtrate was evaporated and the residue was purified on aluminum oxide(basic) affording target compound 10 in 25% yield. MS m/z (%); 83 (54), 68 (32), 56 (100), 42 (61); HRMS calcd for C₄H₇N₂ (M - H)⁺ 83.0609, found 83.0612.