Site-selective benzoin-type cyclization of unsymmetrical dialdoses catalyzed by N-heterocyclic carbenes for divergent cyclitol synthesis

被引：14

作者：

Kang, Bubwoong ^{[1
]}

Wang, Yinli ^{[1
]}

Kuwano, Satoru ^{[1
]}

Yamaoka, Yousuke ^{[1
]}

Takasu, Kiyosei ^{[1
]}

Yamada, Ken-ichi ^{[1
,2
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan

来源：

CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 32期

关键词：

CHIRAL BUILDING-BLOCK; ACYLOIN CONDENSATION; KINETIC RESOLUTION; SECONDARY ALCOHOLS; THIAZOLIUM SALT; LEAVING GROUP; ALDEHYDES; INOSITOLS; QUEBRACHITOL; CONDURITOLS;

D O I：

10.1039/c7cc01191a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly site-selective N-heterocyclic carbene (NHC)-catalyzed benzoin-type cyclization of unsymmetrical dialdoses is developed to enable a divergent cyclitol synthesis. The choice of chiral NHCs and protecting groups affects the site-selectivity. The resulting inososes are converted into epi- ,muco- and myo-inositols, and their chiral protected derivatives are formed in good yields.

引用

页码：4469 / 4472

页数：4

共 50 条

[21] SYNTHESIS OF N-HETEROCYCLIC CARBENE LIGANDS FOR SITE-SELECTIVE C-H ALKYLATION BY COOPERATIVE NICKEL/ALUMINUM CATALYSIS
Okumura, Shogo
Ebara, Tomohiro
Semba, Kazuhiko
Nakao, Yoshiaki
HETEROCYCLES, 2019, 99 (02) : 1128 - 1144
[22] N-heterocyclic carbenes. IV.1synthesis of symmetrical and unsymmetrical imidazolium salts with abietane moiety
Glushkov, V. A.
Arapov, K. A.
Kotelev, M. S.
Rudowsky, K. S.
Suponitsky, K. Yu
Gorbunov, A. A.
Maiorova, O. A.
Slepukhin, P. A.
HETEROATOM CHEMISTRY, 2012, 23 (01) : 5 - 15
[23] Synthesis, Structure, and Catalytic Activity of New Ruthenium(II) Indenylidene Complexes Bearing Unsymmetrical N-Heterocyclic Carbenes
Ablialimov, Osman
Kedziorek, Mariusz
Malinska, Maura
Wozniak, Krzysztof
Grela, Karol
ORGANOMETALLICS, 2014, 33 (09) : 2160 - 2171
[24] Asymmetric synthesis of chromanones via N-heterocyclic carbene catalyzed intramolecular crossed-benzoin reactions
Enders, Dieter
Niemeier, Oliver
Raabe, Gerhard
SYNLETT, 2006, (15) : 2431 - 2434
[25] Improved microwave synthesis of unsymmetrical N,N′-diaryl-1,2-aminoethane and imidazolidinium salts as precursors of N-heterocyclic carbenes
Ibrahim, Yehia A.
Al-Awadi, Nouria A.
Al-Azemi, Talal F.
John, Elizabeth
RSC ADVANCES, 2014, 4 (73): : 38869 - 38876
[26] A Family of Thiazolium Salt Derived N-Heterocyclic Carbenes (NHCs) for Organocatalysis: Synthesis, Investigation and Application in Cross-Benzoin Condensation
Piel, Isabel
Pawelczyk, Marius D.
Hirano, Keiichi
Froehlich, Roland
Glorius, Frank
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (28) : 5475 - 5484
[27] Synthesis and Characterization of New Bulky α-Hydroxy Ketones by N-Heterocyclic Carbene-Catalyzed Intramolecular Benzoin Condensation
Hasdemir, Belma
Alhallak, Abdurrahman
Yildiz, Tuelay
CHEMISTRYSELECT, 2024, 9 (26):
[28] Remote site-selective arene C-H functionalization enabled by N-heterocyclic carbene organocatalysis
Li, Qing-Zhu
Zou, Wen-Lin
Yu, Zhao-Yuan
Kou, Xin-Xin
Liu, Yan-Qing
Zhang, Xiang
He, Yu
Li, Jun-Long
NATURE CATALYSIS, 2024, 7 (08): : 900 - 911
[29] A mechanistic study on the gold(i)-catalyzed cyclization of propargylic amide: revealing the impact of expanded-ring N-heterocyclic carbenes
Ma, Yumiao
Ali, Hafiz Saqib
Hussein, Aqeel A.
CATALYSIS SCIENCE & TECHNOLOGY, 2022, 12 (02) : 674 - 685
[30] Sonogashira-type cross-coupling reactions catalyzed by copper complexes of pincer N-heterocyclic carbenes
Domyati, Doaa
Latifi, Reza
Tahsini, Laleh
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 860 : 98 - 105

← 1 2 3 4 5 →