Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by γ-cyclodextrins with a flexible or rigid cap

Cheng Yang, Asao Nakamura, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticle

60 Citations (Scopus)

Abstract

A series of modified γ-cyclodextrins (CDs) with a flexible or rigid cap, synthesized and used as chiral supramolecular hosts for mediating the enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid, significantly improved the chemical and optical yields of chiral head-to-head cyclodimer 3, while the γ-CD with a rigid cap dramatically inverted the stereochemical outcomes and further improved the enantioselectivities of both head-to-tail and head-to-head dimers 2 and 3.

Original languageEnglish
Pages (from-to)3005-3008
Number of pages4
JournalOrganic Letters
Volume8
Issue number14
DOIs
Publication statusPublished - 2006 Jul 6
Externally publishedYes

Fingerprint

Cyclodextrins
caps
acids
Enantioselectivity
Dimers
dimers
anthracene-1-carboxylic acid

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by γ-cyclodextrins with a flexible or rigid cap. / Yang, Cheng; Nakamura, Asao; Wada, Takehiko; Inoue, Yoshihisa.

In: Organic Letters, Vol. 8, No. 14, 06.07.2006, p. 3005-3008.

Research output: Contribution to journalArticle

@article{23ebffeb38a84cd586c39d1998da12a1,
title = "Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by γ-cyclodextrins with a flexible or rigid cap",
abstract = "A series of modified γ-cyclodextrins (CDs) with a flexible or rigid cap, synthesized and used as chiral supramolecular hosts for mediating the enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid, significantly improved the chemical and optical yields of chiral head-to-head cyclodimer 3, while the γ-CD with a rigid cap dramatically inverted the stereochemical outcomes and further improved the enantioselectivities of both head-to-tail and head-to-head dimers 2 and 3.",
author = "Cheng Yang and Asao Nakamura and Takehiko Wada and Yoshihisa Inoue",
year = "2006",
month = "7",
day = "6",
doi = "10.1021/ol061004x",
language = "English",
volume = "8",
pages = "3005--3008",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "14",

}

TY - JOUR

T1 - Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by γ-cyclodextrins with a flexible or rigid cap

AU - Yang, Cheng

AU - Nakamura, Asao

AU - Wada, Takehiko

AU - Inoue, Yoshihisa

PY - 2006/7/6

Y1 - 2006/7/6

N2 - A series of modified γ-cyclodextrins (CDs) with a flexible or rigid cap, synthesized and used as chiral supramolecular hosts for mediating the enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid, significantly improved the chemical and optical yields of chiral head-to-head cyclodimer 3, while the γ-CD with a rigid cap dramatically inverted the stereochemical outcomes and further improved the enantioselectivities of both head-to-tail and head-to-head dimers 2 and 3.

AB - A series of modified γ-cyclodextrins (CDs) with a flexible or rigid cap, synthesized and used as chiral supramolecular hosts for mediating the enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid, significantly improved the chemical and optical yields of chiral head-to-head cyclodimer 3, while the γ-CD with a rigid cap dramatically inverted the stereochemical outcomes and further improved the enantioselectivities of both head-to-tail and head-to-head dimers 2 and 3.

UR - http://www.scopus.com/inward/record.url?scp=33746625133&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33746625133&partnerID=8YFLogxK

U2 - 10.1021/ol061004x

DO - 10.1021/ol061004x

M3 - Article

VL - 8

SP - 3005

EP - 3008

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 14

ER -