Simplification of the Mitsunobu reaction.: Di-p-chlorobenzyl azodicarboxylate:: A new azodicarboxylate

被引:77
作者
Lipshutz, Bruce H. [1 ]
Chung, David W. [1 ]
Rich, Brian [1 ]
Corral, Ricardo [1 ]
机构
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
关键词
D O I
10.1021/ol0618757
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Di-p-chlorobenzyl azodicarboxylate (DCAD) is introduced as a novel, stable, solid alternative to DEAD and DIAD for a variety of Mitsunobu couplings. DCAD/Ph3P-mediated reactions in CH2Cl2 generate a readily separable hydrazine byproduct.
引用
收藏
页码:5069 / 5072
页数:4
相关论文
共 14 条
[1]   Sulfonation with inversion by Mitsunobu reaction: An improvement on the original conditions [J].
Anderson, NG ;
Lust, DA ;
Colapret, KA ;
Simpson, JH ;
Malley, MF ;
Gougoutas, JZ .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) :7955-7958
[2]   POLYMER-SUPPORTED ALKYL AZODICARBOXYLATES FOR MITSUNOBU REACTIONS [J].
ARNOLD, LD ;
ASSIL, HI ;
VEDERAS, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :3973-3976
[3]  
Czako B., 2005, STRATEGIC APPL NAMED, P294
[4]   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
[5]   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
[6]   Diphenyl 2-pyridylphosphine and di-tert-butyl azodicarboxylate:convenient reagents for the Mitsunobu reaction [J].
Kiankarimi, M ;
Lowe, R ;
McCarthy, JR ;
Whitten, JP .
TETRAHEDRON LETTERS, 1999, 40 (24) :4497-4500
[7]   BENZYL BENZOATES FROM THE ROOT OF UVARIA-PURPUREA [J].
KODPINID, M ;
SADAVONGVIVAD, C ;
THEBTARANONTH, C ;
THEBTARANONTH, Y .
PHYTOCHEMISTRY, 1984, 23 (01) :199-200
[8]  
Li J. J., 2003, NAME REACTIONS, V2nd, P265, DOI [10.1007/978-3-662-05336-2_198, DOI 10.1007/978-3-662-05336-2_198]
[9]   STEREOSPECIFIC AND STEREOSELECTIVE REACTIONS .1. PREPARATION OF AMINES FROM ALCOHOLS [J].
MITSUNOB.O ;
WADA, M ;
SANO, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (02) :679-&
[10]   PREPARATION OF CARBOXYLIC ESTERS AND PHOSPHORIC ESTERS BY ACTIVATION OF ALCOHOLS [J].
MITSUNOBU, O ;
EGUCHI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1971, 44 (12) :3427-+