Chirality transmission in flexible 5,5′-dinitrodiphenic esters connected with chiral secondary alcohols

Shinzo Hosoi, Makiko Kamiya, Fumiyuki Kiuchi, Tomihisa Ohta

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Induced circular dichroism (CD) was observed with dinitrodiphenic esters of chiral secondary alcohols. The CD spectra of the esters prepared from a pair of antipodal alcohols were symmetrical to each other relative to the x-axis, indicating the enantiomeric nature of the esters. The sign of the Cotton effect at around 270 nm was found to reflect the absolute configuration of the original alcohol. In the case of aliphatic mono-alcohols, negative Cotton effect was observed for the esters of (R)-alcohols and a positive effect for the esters of (S)-alcohols. On the contrary, unsaturation or an oxygen atom at the vicinal position reversed the sign of the Cotton effect.

Original languageEnglish
Pages (from-to)6315-6317
Number of pages3
JournalTetrahedron Letters
Volume42
Issue number36
DOIs
Publication statusPublished - 2001 Sep 3
Externally publishedYes

Fingerprint

Chirality
Esters
Alcohols
Cotton
Circular Dichroism
Oxygen
Atoms

Keywords

  • Absolute configuration
  • Alcohols
  • Asymmetric induction
  • Axial chirality
  • Circular dichroism
  • Cotton effect

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Chirality transmission in flexible 5,5′-dinitrodiphenic esters connected with chiral secondary alcohols. / Hosoi, Shinzo; Kamiya, Makiko; Kiuchi, Fumiyuki; Ohta, Tomihisa.

In: Tetrahedron Letters, Vol. 42, No. 36, 03.09.2001, p. 6315-6317.

Research output: Contribution to journalArticle

Hosoi, Shinzo ; Kamiya, Makiko ; Kiuchi, Fumiyuki ; Ohta, Tomihisa. / Chirality transmission in flexible 5,5′-dinitrodiphenic esters connected with chiral secondary alcohols. In: Tetrahedron Letters. 2001 ; Vol. 42, No. 36. pp. 6315-6317.
@article{62f7c4ac724c4e139a20827e42ac564f,
title = "Chirality transmission in flexible 5,5′-dinitrodiphenic esters connected with chiral secondary alcohols",
abstract = "Induced circular dichroism (CD) was observed with dinitrodiphenic esters of chiral secondary alcohols. The CD spectra of the esters prepared from a pair of antipodal alcohols were symmetrical to each other relative to the x-axis, indicating the enantiomeric nature of the esters. The sign of the Cotton effect at around 270 nm was found to reflect the absolute configuration of the original alcohol. In the case of aliphatic mono-alcohols, negative Cotton effect was observed for the esters of (R)-alcohols and a positive effect for the esters of (S)-alcohols. On the contrary, unsaturation or an oxygen atom at the vicinal position reversed the sign of the Cotton effect.",
keywords = "Absolute configuration, Alcohols, Asymmetric induction, Axial chirality, Circular dichroism, Cotton effect",
author = "Shinzo Hosoi and Makiko Kamiya and Fumiyuki Kiuchi and Tomihisa Ohta",
year = "2001",
month = "9",
day = "3",
doi = "10.1016/S0040-4039(01)01241-2",
language = "English",
volume = "42",
pages = "6315--6317",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "36",

}

TY - JOUR

T1 - Chirality transmission in flexible 5,5′-dinitrodiphenic esters connected with chiral secondary alcohols

AU - Hosoi, Shinzo

AU - Kamiya, Makiko

AU - Kiuchi, Fumiyuki

AU - Ohta, Tomihisa

PY - 2001/9/3

Y1 - 2001/9/3

N2 - Induced circular dichroism (CD) was observed with dinitrodiphenic esters of chiral secondary alcohols. The CD spectra of the esters prepared from a pair of antipodal alcohols were symmetrical to each other relative to the x-axis, indicating the enantiomeric nature of the esters. The sign of the Cotton effect at around 270 nm was found to reflect the absolute configuration of the original alcohol. In the case of aliphatic mono-alcohols, negative Cotton effect was observed for the esters of (R)-alcohols and a positive effect for the esters of (S)-alcohols. On the contrary, unsaturation or an oxygen atom at the vicinal position reversed the sign of the Cotton effect.

AB - Induced circular dichroism (CD) was observed with dinitrodiphenic esters of chiral secondary alcohols. The CD spectra of the esters prepared from a pair of antipodal alcohols were symmetrical to each other relative to the x-axis, indicating the enantiomeric nature of the esters. The sign of the Cotton effect at around 270 nm was found to reflect the absolute configuration of the original alcohol. In the case of aliphatic mono-alcohols, negative Cotton effect was observed for the esters of (R)-alcohols and a positive effect for the esters of (S)-alcohols. On the contrary, unsaturation or an oxygen atom at the vicinal position reversed the sign of the Cotton effect.

KW - Absolute configuration

KW - Alcohols

KW - Asymmetric induction

KW - Axial chirality

KW - Circular dichroism

KW - Cotton effect

UR - http://www.scopus.com/inward/record.url?scp=0035801836&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035801836&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)01241-2

DO - 10.1016/S0040-4039(01)01241-2

M3 - Article

AN - SCOPUS:0035801836

VL - 42

SP - 6315

EP - 6317

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 36

ER -