Abstract
Chiral aziridines 5, 6 and enamine 7 were synthesised; compounds B, C and D, which were obtained over 100 years ago, were not aziridines; the product described as B was identified with isomeric enamine 7. The crystal structures of aziridines (±)- and (+)-6 were studied.
References
1.
NAGANAWA H., USUI N., TAKITA T., HAMADA M., UMEZAWA H.
Journal of Antibiotics,
2012
2.
10.1070/MC2003v013n05ABEH001806_bib1_2
Umezawa
Japan Pat.,
1977
3.
FURUKAWA N., OAE S., YOSHIMURA T.
Synthesis,
1976
4.
Legters J., Thijs L., Zwanenburg B.
Tetrahedron,
1991
5.
6.
10.1070/MC2003v013n05ABEH001806_bib1_6
Gawronski
Tartaric, Maleic Acids in Synthesis. A Source Book of Building Blocks, Ligands, Auxiliaries Resolving Agents,
1999
7.
10.1070/MC2003v013n05ABEH001806_bib2_1
Lehrfeld
Ber. Dtsch. Chem. Ges.,
1816
8.
Hell C., Poliakoff R.
Berichte der deutschen chemischen Gesellschaft,
1892
9.
Claus A., Voeller F.
Berichte der deutschen chemischen Gesellschaft,
1881
10.
Berlin K.D., Williams L.G., Dermer O.C.
Tetrahedron Letters,
1968
11.
Harada K., Nakamura I.
Chemistry Letters,
1978
12.
10.1070/MC2003v013n05ABEH001806_bib3_3
Trapenzieris
Khim. Geterotsikl. Soedin.,
1983
13.
10.1070/MC2003v013n05ABEH001806_bib3_4
Chervin
Izv. Akad. Nauk SSSR, Ser. Khim.,
1988
14.
Bucciarelli M., Forni A., Moretti I., Prati F., Torre G.
Journal of the Chemical Society Perkin Transactions 1,
1993
15.
10.1070/MC2003v013n05ABEH001806_bib4
Dermer
Ethyleneimine, Other Aziridines. Chemistry Applications,
1969
16.
Carr R.M., Norman R.O., Vernon J.M.
Journal of the Chemical Society Chemical Communications,
1977
17.
10.1070/MC2003v013n05ABEH001806_bib5_2
Moskalenko
Izv. Akad. Nauk, Ser. Khim.,
1992
18.
Lohray B.B., Ahuja J.R.
Journal of the Chemical Society Chemical Communications,
1991
19.
Stereochemistry and chiroptical properties of the nonplanar nitrosamine group in N-nitrosoaziridines
Shustov G.V., Kachanov A.V., Kadorkina G.K., Kostyanovskii R.G., Rauk A.
Journal of the American Chemical Society,
1992
20.
10.1070/MC2003v013n05ABEH001806_bib7
Zaichenko
Izv. Akad. Nauk SSSR, Ser. Khim.,
1988
21.
Gabriel S.
Berichte der deutschen chemischen Gesellschaft,
1888
22.
Howard C.C., Marckwald W.
Berichte der deutschen chemischen Gesellschaft,
1899
23.
Marckwald W.
Berichte der deutschen chemischen Gesellschaft,
1900
24.
Ripoll J.L., Lebrun H., Thuillier A.
Tetrahedron,
1980
25.
10.1070/MC2003v013n05ABEH001806_bib9
Shtamburg
Izv. Akad. Nauk SSSR, Ser. Khim.,
1981
26.
Drenkard S., Ferris J., Eschenmoser A.
Helvetica Chimica Acta,
1990