Highly regioselective transformation of alkenyl bromides into α-bromoaziridines and α-bromohydrazones

被引：36

作者：

Krasnova, LB ^{[1
]}

Yudin, AK ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 10期

关键词：

D O I：

10.1021/ol060336z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthetic utility of alpha.-halohydrazones is an underexplored area due to the lack of chemo- and regloselective routes towards these molecules. Herein, we describe a general method for alpha-bromohydrazone synthesis via the rearrangement of alpha-bromoaziridines, which can be readily prepared for the first time from the corresponding alkenyl bromides. The rearrangement of alpha-bromoaziridines into alpha-bromohydrazones proceeds with high yields and with high selectivities.

引用

页码：2011 / 2014

页数：4

共 37 条

[11] NUCLEOPHILIC DISPLACEMENTS ON 3-MEMBERED RINGS [J].

DEYRUP, JA ;

GREENWAL.RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (20) :4538-&

[12]

Drozdova T.I., 1999, Russ. Chem. Rev, V68, P581, DOI [DOI 10.1070/RC1999V068N07ABEH000476, 10.1070/RC1999v068n07ABEH000476]

[13]

DUHAMEL L, 1974, TETRAHEDRON LETT, V15, P3167

[14]

DUHAMEL P, 1973, TETRAHEDRON LETT, V14, P1339

[15]

Eicher TS, 2013, The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications

[16]

FIELDS EK, 1959, CHEM IND-LONDON, P1216

[17]

Fields R., 1969, J CHEM SOC C, V1, P165

[18] PRACTICAL PROCEDURE FOR THE PREPARATION OF HINDERED ALPHA-HALOEPOXIDES AND ALPHA-HALOALDEHYDES [J].

GRALAK, J ;

VALNOT, JY .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1979, 11 (3-4) :107-110

[19]

KHLEBNIKOV AF, 1990, KHIM GETEROTSIKL+, P1086

[20]

Kobrich G., 1969, Tetrahedron Lett, V10, P2181, DOI [10.1016/S0040-4039(01)88116-8, DOI 10.1016/S0040-4039(01)88116-8]

← 1 2 3 4 →