Strictly diastereocontrolled photocyclodimerization of 2-anthracenecarboxylates tethered to cyclic tetrasaccharides

Photocyclodimerization of 2-anthracenecarboxylate tethered to a cyclic nigerosylnigerose scaffold gave a single chiral cyclodimer (out of two achiral and two chiral stereoisomers) in 99% optical and 96% chemical yields, achieving the ultimate stereocontrol of the supramolecular photochirogenesis in...

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Published inChemical communications (Cambridge, England) Vol. 48; no. 73; pp. 9156 - 9158
Main Authors Fukuhara, Gaku, Nakamura, Tomohiro, Kawanami, Yuko, Yang, Cheng, Mori, Tadashi, Hiramatsu, Hiroyuki, Dan-oh, Yasufumi, Tsujimoto, Kazuo, Inoue, Yoshihisa
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2012
Subjects
Anthracenes - chemistry
Aqueous solutions
Carboxylic Acids - chemistry
Chemistry
Chemistry, Multidisciplinary
Cyclization
Dimerization
Glucans - chemistry
Models, Molecular
Photochemical Processes
Physical Sciences
Scaffolds
Science & Technology
Stereoisomerism
DIASTEREODIFFERENTIATING PHOTOCYCLODIMERIZATION
INTRAMOLECULAR 2+2 PHOTOCYCLOADDITION
GAMMA-CYCLODEXTRIN
ANTHRACENE
INDUCTION
PHOTOCHEMICAL-REACTIONS
PHOTOCHIROGENESIS
PHOTODIMERIZATION
IDENTIFICATION
SCAFFOLD
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Summary:Photocyclodimerization of 2-anthracenecarboxylate tethered to a cyclic nigerosylnigerose scaffold gave a single chiral cyclodimer (out of two achiral and two chiral stereoisomers) in 99% optical and 96% chemical yields, achieving the ultimate stereocontrol of the supramolecular photochirogenesis in aqueous solution at 25 degrees C.
Bibliography:KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc34880b