Tartaric acid and its acyl derivatives. Part 5. Direct synthesis of monoacyltartaric acids and novel mono(benzoyl)tartaric anhydride: unusual findings in tartaric acid acylation

被引：7

作者：

Bernas, Urszula ^{[1
]}

Hajmowicz, Halina ^{[1
]}

Madura, Izabela D. ^{[1
]}

Majcher, Monika ^{[1
]}

Synoradzki, Ludwik ^{[1
]}

Zawada, Krzysztof ^{[1
]}

机构：

[1] Warsaw Univ Technol, Fac Chem, Ul Noakowskiego 3, PL-00664 Warsaw, Poland

来源：

ARKIVOC | 2010年

关键词：

Acylation; chiral pool; hydroxycarboxylic acids; tartaric acid; CHIRAL (ACYLOXY)BORANE COMPLEX; DIELS-ALDER REACTION; CAB; CATALYSIS; ALCOHOLS; ANALOGS;

D O I：

10.3998/ark.5550190.0011.b01

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Practical acylation of unprotected tartaric acid 1 by acyl chlorides to the corresponding monoacyltartaric acids 2 has been shown. Several unusual cases in the acylation of 1 are observed; it has been found that two routes of acylation are possible. In the benzoylation of 1, in addition to the expected products, the formation of a previously undescribed monobenzoyltartaric anhydride 7a is reported. An unusual DME cleavage during the course of acylation was also observed.

引用

页码：1 / 12

页数：12

共 37 条

[1] ANSCHUTZ R, 1880, BER, V13, P1175
[2] SELECTIVE AMINOLYSIS OF BENZOATES AND ACETATES OF ALPHA-HYDROXY ACIDS AND PHENOLS WITH BENZYLAMINE AND BUTAN-1-AMINE
BELL, KH
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1987, 40 (10) : 1723 - 1735
[3] Synthesis and chiroptical properties of a new type of chiral depsipeptide dendrons
Buschhaus, B
Bauer, W
Hirsch, A
[J]. TETRAHEDRON, 2003, 59 (22) : 3899 - 3915
[4] Time dependent efficiency of optical resolution of aminooxiranes with O,O′-dibenzoyl-(R,R)-tartaric acid
Faigl, F
Thurner, A
Farkas, F
Proszenyák, A
Valacchi, M
Mordini, A
[J]. ARKIVOC, 2004, : 53 - 59
[5] FAIGL F, 1985, Patent No. 34720
[6] FURUTA H, 1998, J AM CHEM SOC, V110, P6254
[7] CHIRAL (ACYLOXY)BORANE (CAB) - A POWERFUL AND PRACTICAL CATALYST FOR ASYMMETRIC DIELS-ALDER REACTIONS
FURUTA, K
SHIMIZU, S
MIWA, Y
YAMAMOTO, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) : 1481 - 1483
[8] FURUTA K, 1995, ORG SYNTH, V72, P86
[9] CATALYTIC ASYMMETRIC ALDOL REACTIONS - USE OF A CHIRAL (ACYLOXY)BORANE COMPLEX AS A VERSATILE LEWIS ACID CATALYST
FURUTA, K
MARUYAMA, T
YAMAMOTO, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) : 1041 - 1042
[10] ASYMMETRIC HETERO-DIELS-ALDER REACTION CATALYZED BY STABLE AND EASILY PREPARED CAB CATALYSTS
GAO, QZ
ISHIHARA, K
MARUYAMA, T
MOURI, M
YAMAMOTO, H
[J]. TETRAHEDRON, 1994, 50 (04) : 979 - 988

← 1 2 3 4 →