A SYNTHESIS OF β-ALLYL SUBSTITUTED ISOTETRONIC ACID DERIVATIVES VIA THERMAL CLAISEN REARRANGEMENT

被引：2

作者：

Ma, Xiaping ^{[1
]}

Li, Zhiming ^{[1
]}

Wang, Quanrui ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

来源：

HETEROCYCLES | 2010年 / 81卷 / 06期

关键词：

2-(5H)-Furanone; Butenolide; 3,3] Sigmatropic Rearrangement; Allyl Vinyl Ether; Conia-Ene Reaction; ETHYL PYRUVATE;

D O I：

10.3987/COM-10-11937

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Isotetronic acids are of great interest in agricultural and pharmacological research and occur in a number of natural products. This paper describes the first Claisen rearrangement of the O-allyl substituted isotetronic acids 2 under thermal conditions furnishing the beta-allyl substituted isotetronic acid derivatives 3 in high yields.

引用

页码：1485 / 1491

页数：7

共 50 条

[21] SUBSTITUENT EFFECTS ON THE ALIPHATIC CLAISEN REARRANGEMENT .1. SYNTHESIS AND REARRANGEMENT OF CYANO-SUBSTITUTED ALLYL VINYL ETHERS
BURROWS, CJ
CARPENTER, BK
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (23) : 6983 - 6984
[22] THIOKETENE SYNTHESES .5. ALLYL-SUBSTITUTED THIOKETENES VIA THIO-CLAISEN REARRANGEMENT
SCHAUMANN, E
GRABLEY, FF
LIEBIGS ANNALEN DER CHEMIE, 1979, (11): : 1746 - 1755
[23] CLAISEN REARRANGEMENT OF ALLYL ETHYL KETENE ACETALS GENERATED INSITU VIA BENZENESELENENIC ACID ELIMINATION
PITTELOUD, R
PETRZILKA, M
HELVETICA CHIMICA ACTA, 1979, 62 (04) : 1319 - 1325
[24] Synthesis of Allyl Acetals and Their Catalytic Claisen-Cope Rearrangement
Nakabayashi, Kazuhiro
Ooho, Masato
Niino, Teppei
Kitamura, Tsugio
Yamaji, Teizo
Bulletin of the Chemical Society of Japan, 2004, 77 (01): : 157 - 164
[25] Synthesis of allyl acetals and their catalytic Claisen-Cope rearrangement
Nakabayashi, K
Ooho, M
Niino, T
Kitamura, T
Yamaji, T
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (01) : 157 - 164
[26] Enantioselective synthesis of beta-substituted butyric acid derivatives via orthoester Claisen rearrangement of enzymatically resolved allylic alcohols: application to the synthesis of (R)-(-)-baclofen
Brenna, E
Caraccia, N
Fuganti, C
Fuganti, D
Grasselli, P
TETRAHEDRON-ASYMMETRY, 1997, 8 (22) : 3801 - 3805
[27] CLAISEN REARRANGEMENT .3. PARA CLAISEN REARRANGEMENT TO NITROGEN IN ALLYL 3-SUBSTITUTED 4-QUIMOLYL ETHERS
MAKISUMI, Y
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (06): : 1986 - &
[28] ACYCLIC STEREOCONTROL VIA THE CLAISEN REARRANGEMENT - A FORMAL SYNTHESIS OF (+) TIRANDAMYCIC ACID
ZIEGLER, FE
WESTER, RT
TETRAHEDRON LETTERS, 1984, 25 (06) : 617 - 620
[29] Stereoselective synthesis of β-branched phenylalanine derivatives via chelate-claisen rearrangement
Quirin, Christian
Kazmaier, Uli
Synthesis, 2009, (10) : 1725 - 1731
[30] Stereoselective Synthesis of β-Branched Phenylalanine Derivatives via Chelate-Claisen Rearrangement
Quirin, Christian
Kazmaier, Uli
SYNTHESIS-STUTTGART, 2009, (10): : 1725 - 1731

← 1 2 3 4 5 →