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200517.fm Page 119 Friday, March 18, 2005 2:52 PM
2005
Aziridine derivatives
R 0040
Propargylic Carbenoids. Part 4. High Kinetic Resolution in the Addition of a
Allenylzinc onto Enantiopure N-tert-Butanesulfinimines: Concise Syn17- 109 Racemic
thesis of Enantiopure trans-2-Ethynylaziridines. — Treatment of enantiopure
N-tert-butanesulfinimines with the allene (II) offers a convenient route to chiral alkynylaziridines. Excellent stereoselectivity is observed which results from kinetic resolution of a chelation-type transition state. Unfortunately, deprotection of the aziridines
(Vd)-(Vf) is unsuccessful. In these cases, aziridine ring opening takes place. —
(CHEMLA, F.; FERREIRA*, F.; J. Org. Chem. 69 (2004) 24, 8244-8250; Lab. Chim.
Org., CNRS, Univ. P. et M. Curie, F-75252 Paris, Fr.; Eng.) — Jannicke
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