Stereocontrol of molecular jump-rope

Crystallization-induced asymmetric transformation of planar-chiral cyclophanes

Nobuhiro Kanomata, Yoshiharu Ochiai

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Stereocontrol of planar-type cyclophanes was achieved by crystallization-induced asymmetric transformation in a molten state. Simply heating a 1/1 mixture of the solid and the liquid diastereoisomers of the bridged nicotinamides (S,3′S)-1 and (R,3′S)-2 effected the disequilibriation via rope-skipping isomerization to the solid sides, giving (S,3′S)-1 with up to 99% de.

Original languageEnglish
Pages (from-to)1045-1048
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number6
DOIs
Publication statusPublished - 2001 Feb 5
Externally publishedYes

Fingerprint

Niacinamide
Crystallization
Heating
Isomerization
Molten materials
Liquids

Keywords

  • Crystallization-induced asymmetric transformation
  • Cyclophanes
  • Planar chirality
  • Rope-skipping isomerization
  • Stereocontrol

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereocontrol of molecular jump-rope : Crystallization-induced asymmetric transformation of planar-chiral cyclophanes. / Kanomata, Nobuhiro; Ochiai, Yoshiharu.

In: Tetrahedron Letters, Vol. 42, No. 6, 05.02.2001, p. 1045-1048.

Research output: Contribution to journalArticle

@article{0788c56baa534c1e82f5676d97d82ee0,
title = "Stereocontrol of molecular jump-rope: Crystallization-induced asymmetric transformation of planar-chiral cyclophanes",
abstract = "Stereocontrol of planar-type cyclophanes was achieved by crystallization-induced asymmetric transformation in a molten state. Simply heating a 1/1 mixture of the solid and the liquid diastereoisomers of the bridged nicotinamides (S,3′S)-1 and (R,3′S)-2 effected the disequilibriation via rope-skipping isomerization to the solid sides, giving (S,3′S)-1 with up to 99{\%} de.",
keywords = "Crystallization-induced asymmetric transformation, Cyclophanes, Planar chirality, Rope-skipping isomerization, Stereocontrol",
author = "Nobuhiro Kanomata and Yoshiharu Ochiai",
year = "2001",
month = "2",
day = "5",
doi = "10.1016/S0040-4039(00)02043-8",
language = "English",
volume = "42",
pages = "1045--1048",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "6",

}

TY - JOUR

T1 - Stereocontrol of molecular jump-rope

T2 - Crystallization-induced asymmetric transformation of planar-chiral cyclophanes

AU - Kanomata, Nobuhiro

AU - Ochiai, Yoshiharu

PY - 2001/2/5

Y1 - 2001/2/5

N2 - Stereocontrol of planar-type cyclophanes was achieved by crystallization-induced asymmetric transformation in a molten state. Simply heating a 1/1 mixture of the solid and the liquid diastereoisomers of the bridged nicotinamides (S,3′S)-1 and (R,3′S)-2 effected the disequilibriation via rope-skipping isomerization to the solid sides, giving (S,3′S)-1 with up to 99% de.

AB - Stereocontrol of planar-type cyclophanes was achieved by crystallization-induced asymmetric transformation in a molten state. Simply heating a 1/1 mixture of the solid and the liquid diastereoisomers of the bridged nicotinamides (S,3′S)-1 and (R,3′S)-2 effected the disequilibriation via rope-skipping isomerization to the solid sides, giving (S,3′S)-1 with up to 99% de.

KW - Crystallization-induced asymmetric transformation

KW - Cyclophanes

KW - Planar chirality

KW - Rope-skipping isomerization

KW - Stereocontrol

UR - http://www.scopus.com/inward/record.url?scp=0035808866&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035808866&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)02043-8

DO - 10.1016/S0040-4039(00)02043-8

M3 - Article

VL - 42

SP - 1045

EP - 1048

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 6

ER -