Improved Synthesis of Racemate and Enantiomers of Taniguchi Lactone and Conversion of Their C-C Double Bonds into Triple Bonds

被引：5

作者：

Krizkova, Petra Malova ^{[1
]}

Lindner, Wolfgang ^{[2
]}

Hammerschmidt, Friedrich ^{[1
]}

机构：

[1] Univ Vienna, Inst Organ Chem, Fac Chem, Wahringerstr 38, A-1090 Vienna, Austria

[2] Univ Vienna, Inst Analyt Chem, Fac Chem, Wahringerstr 38, A-1090 Vienna, Austria

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 03期

关键词：

alkynes; chiral resolution; electrocyclic reaction; halogenation; acetals; lactones; STEREOSELECTIVE TOTAL-SYNTHESIS; DIMETHYL (DIAZOMETHYL)PHOSPHONATE; ABSOLUTE-CONFIGURATION; ALDEHYDES; REAGENT; ALKYNES; GENERATION;

D O I：

10.1055/s-0036-1591516

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

cis-2-Butene-1,4-diol was heated with triethyl orthoacetate and p-hydroquinone as catalyst at 170 degrees C to give racemic Taniguchi lactone. It was converted into diastereomeric amides with (S)-1-phenylethylamine for stereoisomer resolution. The double bonds of (+/-)-, (R)- and (S)-Taniguchi lactones were brominated and dehydrobrominated in two steps, using at first DBU and then LDA, to deliver the triple bonds.

引用

页码：651 / 657

页数：7

共 50 条

[21] POLYMERS WITH THERMOSENSITIVE C-C BONDS
BRAUN, D
KUHN, KJ
MEID, H
HELLMANN, EH
HELLMANN, GP
JOURNAL OF POLYMER MATERIALS, 1994, 11 (03): : 197 - 205
[22] Interpolymers with conjugated C-C bonds
Vointseva, II
Gilman, LM
Valetskii, PM
VYSOKOMOLEKULYARNYE SOEDINENIYA SERIYA A & SERIYA B, 1997, 39 (11): : 1767 - 1773
[23] SYNTHESIS C-C single bonds made in familiar way
Boerner, Leigh Krietsch
CHEMICAL & ENGINEERING NEWS, 2021, 99 (29) : 13 - 13
[24] Widening the road for C-C bonds
Ritter, SK
CHEMICAL & ENGINEERING NEWS, 2002, 80 (05) : 26 - 27
[25] FORMING ASYMMETRIC C-C BONDS
ENDERS, D
CHEMTECH, 1981, 11 (08) : 504 - 513
[26] Overlong C-C single bonds
Kaupp, G
Boy, J
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2): : 48 - 49
[27] Widening the road for C-C bonds
Ritter, Stephen K.
Chemical and Engineering News, 2002, 80 (05): : 26 - 27
[28] INTRAMOLECULAR MICHAEL AND ANTI-MICHAEL ADDITIONS TO C-C TRIPLE BONDS
SCHWARZ, R
RUDORF, W
ZEITSCHRIFT FUR CHEMIE, 1988, 28 (07): : 265 - 265
[29] Palladium-Catalyzed Bisolefination of C-C Triple Bonds: A Facile Method for the Synthesis of Naphthalene Derivatives
Feng, Chao
Loh, Teck-Peng
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (50) : 17710 - 17712
[30] Copper-catalyzed borylative aminomethylation of C-C double and triple bonds with N,O-acetal
Qiu, Xianfan
Xu, Liugen
Wang, Shuxia
Dai, Ying
Feng, Yunqiu
Gong, Chang
Tao, Chuanzhou
CHEMICAL COMMUNICATIONS, 2021, 57 (26) : 3279 - 3282

← 1 2 3 4 5 →