Formation of scalemic aziridines via the nucleophilic opening of aziridines

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2671-2674

  Bergmeier, Stephen C ^a   Seth, Punit P ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000941580     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo962307f     Document Type: Article

References (47)

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38. e (0.5-0.6 mL). In the case of 11a and 23, the doublet at 1.05 ppm, corresponding to one of the methylene protons on the aziridine ring, was shifted to 1.46 ppm for 23 (S enantiomer) and 1.44 ppm for 11a (R enantiomer).
39. This di-opening product is seen to a small extent with all of the organocuprate reagents (5-10%), but due to the small size of the methylcuprate, increased amounts are seen (up to 25-30%). The amount of di-opening product formed was reduced when the reaction was not allowed to warm to rt and quenched at -78 °C. Warming the reaction to rt also resulted in some loss of optical purity of the products. The aziridines formed in this manner had ee in the range of 92-95%.
40. 15 in 36% yield from dihydropyran in a single step. The olefins formed by this coupling reaction predominantly have the Z configuration.
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46. Compound 9 was prepared by the method of Fujii et al.' These workers prepared the S enantiomer of 9 starting from (R) -serine. We started from natural (S)-serine to prepare compound 9 which was identical in all respects to the enantiomer reported in ref 7 except for the optical rotation [a]D +29.9° (c9.9, EtOAc), which was the opposite.
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