Stereocontrol of molecular jump-rope: Crystallization-induced asymmetric transformation of planar-chiral cyclophanes

Nobuhiro Kanomata; Yoshiharu Ochiai

doi:10.1016/S0040-4039(00)02043-8

Stereocontrol of molecular jump-rope: Crystallization-induced asymmetric transformation of planar-chiral cyclophanes

Nobuhiro Kanomata^*, Yoshiharu Ochiai

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

41 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 language	English
Pages (from-to)	1045-1048
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	6
DOIs	https://doi.org/10.1016/S0040-4039(00)02043-8
Publication status	Published - 2001 Feb 5
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)02043-8

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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",

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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

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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Stereocontrol of molecular jump-rope: Crystallization-induced asymmetric transformation of planar-chiral cyclophanes

Abstract

Keywords

ASJC Scopus subject areas

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