Synchronized stereocontrol of planar chirality by crystallization-induced asymmetric transformation

Nobuhiro Kanomata; Gou Mishima; Jun Onozato

doi:10.1016/j.tetlet.2008.11.021

Synchronized stereocontrol of planar chirality by crystallization-induced asymmetric transformation

Nobuhiro Kanomata^*, Gou Mishima, Jun Onozato

^*Corresponding author for this work

School of Advanced Science and Engineering

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

20 Citations (Scopus)

Abstract

Synchronized stereocontrol of two planar-chiral units was accomplished by using crystallization-induced asymmetric transformation (CIAT) of cyclophane-type bridged bisnicotinate derivatives 5b and 7. After screening various linkers, (S)-2-amino-1-butanol and (S)-tert-leucinol were found to be the most effective for CIAT of the corresponding bridged bisnicotinate 5b and 7, respectively, whose diastereomeric ratio finally reached 97% and 88%, respectively.

Original language	English
Pages (from-to)	409-412
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	4
DOIs	https://doi.org/10.1016/j.tetlet.2008.11.021
Publication status	Published - 2009 Jan 28

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2008.11.021

Cite this

@article{3ba57178315b4d6a8a87267462a76320,

title = "Synchronized stereocontrol of planar chirality by crystallization-induced asymmetric transformation",

abstract = "Synchronized stereocontrol of two planar-chiral units was accomplished by using crystallization-induced asymmetric transformation (CIAT) of cyclophane-type bridged bisnicotinate derivatives 5b and 7. After screening various linkers, (S)-2-amino-1-butanol and (S)-tert-leucinol were found to be the most effective for CIAT of the corresponding bridged bisnicotinate 5b and 7, respectively, whose diastereomeric ratio finally reached 97% and 88%, respectively.",

author = "Nobuhiro Kanomata and Gou Mishima and Jun Onozato",

note = "Funding Information: The authors acknowledge The Asahi Glass Foundation for financial support to this work. ",

year = "2009",

month = jan,

day = "28",

doi = "10.1016/j.tetlet.2008.11.021",

language = "English",

volume = "50",

pages = "409--412",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "4",

}

TY - JOUR

T1 - Synchronized stereocontrol of planar chirality by crystallization-induced asymmetric transformation

AU - Kanomata, Nobuhiro

AU - Mishima, Gou

AU - Onozato, Jun

N1 - Funding Information: The authors acknowledge The Asahi Glass Foundation for financial support to this work.

PY - 2009/1/28

Y1 - 2009/1/28

N2 - Synchronized stereocontrol of two planar-chiral units was accomplished by using crystallization-induced asymmetric transformation (CIAT) of cyclophane-type bridged bisnicotinate derivatives 5b and 7. After screening various linkers, (S)-2-amino-1-butanol and (S)-tert-leucinol were found to be the most effective for CIAT of the corresponding bridged bisnicotinate 5b and 7, respectively, whose diastereomeric ratio finally reached 97% and 88%, respectively.

AB - Synchronized stereocontrol of two planar-chiral units was accomplished by using crystallization-induced asymmetric transformation (CIAT) of cyclophane-type bridged bisnicotinate derivatives 5b and 7. After screening various linkers, (S)-2-amino-1-butanol and (S)-tert-leucinol were found to be the most effective for CIAT of the corresponding bridged bisnicotinate 5b and 7, respectively, whose diastereomeric ratio finally reached 97% and 88%, respectively.

UR - http://www.scopus.com/inward/record.url?scp=57149140845&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=57149140845&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2008.11.021

DO - 10.1016/j.tetlet.2008.11.021

M3 - Article

AN - SCOPUS:57149140845

SN - 0040-4039

VL - 50

SP - 409

EP - 412

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 4

ER -

Synchronized stereocontrol of planar chirality by crystallization-induced asymmetric transformation

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this