Di-2-methoxyethyl azodicarboxylate (DMEAD): An inexpensive and separation-friendly alternative reagent for the Mitsunobu reaction

被引:61
作者
Sugimura, Takashi [1 ]
Hagiya, Kazutake [1 ]
机构
[1] Univ Hyogo, Himeji Inst Technol, Grad Sch Mat Sci, Kamigori, Hyogo 6781297, Japan
关键词
D O I
10.1246/cl.2007.566
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Di-2-methoxyethyl azodicarboxylate (DMEAD) was prepared as an alternative of DEAD or DIAD for the Mitsunobu reaction. Removal of the hydrazinedicarboxylate generated from DMEAD becomes much easier owing to the polar and water-soluble property.
引用
收藏
页码:566 / 567
页数:2
相关论文
共 12 条
[1]   Impurity annihilation:: Chromatography-free parallel Mitsunobu reactions [J].
Barrett, AGM ;
Roberts, RS ;
Schröder, J .
ORGANIC LETTERS, 2000, 2 (19) :2999-3001
[2]  
Carpino L. A., 1973, ORG SYNTH COLL, V5, P160
[3]   Separation-friendly Mitsunobu reactions: A microcosm of recent developments in separation strategies [J].
Dandapani, S ;
Curran, DP .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (13) :3130-3138
[4]   Recent advances in the Mitsunobu reaction: Modified reagents and the quest for chromatography-free separation [J].
Dembinski, R .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (13) :2763-2772
[5]  
Hughes D.L., 1992, ORG REACT, V42, P335, DOI [DOI 10.1002/0471264180.OR042.02, 10.1002/0471264180.OR042.02]
[6]  
Kauer J. C., 1963, ORG SYNTH, V4, P411
[7]   Simplification of the Mitsunobu reaction.: Di-p-chlorobenzyl azodicarboxylate:: A new azodicarboxylate [J].
Lipshutz, Bruce H. ;
Chung, David W. ;
Rich, Brian ;
Corral, Ricardo .
ORGANIC LETTERS, 2006, 8 (22) :5069-5072
[8]   PREPARATION OF ESTERS OF CARBOXYLIC AND PHOSPHORIC ACID VIA QUATERNARY PHOSPHONIUM SALTS [J].
MITSUNOBU, O ;
YAMADA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (10) :2380-+
[9]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[10]   Tetraarylphosphonium salts as solubility-control groups: Phosphonium-supported triphenylphosphine and azodicarboxylate reagents [J].
Poupon, JC ;
Boezio, AA ;
Charette, AB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (09) :1415-1420