Unusual reaction of β-hydroxy α-diazo carbonyl compounds with TsNHN=CHCOCl/Et3N

被引:13
作者
Shi, WF [1 ]
Zhang, B [1 ]
Liu, B [1 ]
Xu, F [1 ]
Xiao, FP [1 ]
Zhang, H [1 ]
Zhang, SW [1 ]
Wang, JB [1 ]
机构
[1] Peking Univ, Coll Chem, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/j.tetlet.2004.04.037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of beta-hydroxy alpha-diazo carbonyl compounds with TsNHN=CHCOCl/Et3N gave beta-(p-tolylsulfonyl) alpha,beta-unsaturated carbonyl compounds or beta-(p-tolylsulfonyl) alpha-diazo esters. The reaction mechanism is discussed. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4563 / 4566
页数:4
相关论文
共 26 条
[1]  
BURKOTH TL, 1969, TETRAHEDRON LETT, V10, P5049
[2]   Competition between Wolff rearrangement and 1,2-hydrogen shift in β-oxy-α-ketocarbenes:: Electrostatic and specific solvent effects [J].
Calvo-Losada, S ;
Suárez, D ;
Sordo, TL ;
Quirante, JJ .
JOURNAL OF PHYSICAL CHEMISTRY B, 1999, 103 (34) :7145-7150
[3]   USE OF RADICAL RING-OPENING FOR INTRODUCTION OF ALKYL AND SUBSTITUTED ALKYL-GROUPS WITH STEREOCHEMICAL CONTROL - A SYNTHETIC APPLICATION OF CYCLOPROPYLCARBINYL RADICALS [J].
CLIVE, DLJ ;
DAIGNEAULT, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3801-3814
[4]   EFFICIENT SYNTHESIS AND INTRAMOLECULAR CYCLOPROPANATION OF UNSATURATED DIAZOACETIC ESTERS [J].
COREY, EJ ;
MYERS, AG .
TETRAHEDRON LETTERS, 1984, 25 (33) :3559-3562
[5]   TOTAL SYNTHESIS OF (+/-)-ANTHERIDIUM-INDUCING FACTOR (AAN,2) OF THE FERN ANEMIA PHYLLITIDIS - CLARIFICATION OF STEREOCHEMISTRY [J].
COREY, EJ ;
MYERS, AG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) :5574-5576
[6]  
Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
[7]   THEORETICAL PREDICTIONS OF ACTIVATION-ENERGIES FOR 1,2-HYDROGEN SHIFTS IN SINGLET CARBENES [J].
EVANSECK, JD ;
HOUK, KN .
JOURNAL OF PHYSICAL CHEMISTRY, 1990, 94 (14) :5518-5523
[8]   PREPARATION AND DECOMPOSITION OF UNSATURATED ESTERS OF DIAZOACETIC ACID [J].
HOUSE, HO ;
BLANKLEY, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01) :53-&
[9]   Investigation of the transition-metal- and acid-catalyzed reactions of β-(N-tosyl)amino diazo carbonyl compounds [J].
Jiang, N ;
Ma, ZH ;
Qu, ZH ;
Xing, XY ;
Xie, LF ;
Wang, JB .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :893-900
[10]   DBU-promoted condensation of acyldiazomethanes to aldehydes and imines under catalytic conditions [J].
Jiang, N ;
Wang, JB .
TETRAHEDRON LETTERS, 2002, 43 (07) :1285-1287