Diastereomeric process-based chiral resolution of helical quinone derivatives using (−)-menthyl chloroformate

Mohammad Shahabuddin; Md Sharif Hossain; Takao Kimura; Michinori Karikomi

doi:10.1016/j.tetlet.2017.10.027

Diastereomeric process-based chiral resolution of helical quinone derivatives using (−)-menthyl chloroformate

Mohammad Shahabuddin, Md Sharif Hossain, Takao Kimura, Michinori Karikomi

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

6 Citations (Scopus)

Abstract

Diastereomeric resolution of helically distorted polycondensed bisphenols (1,1′-bibenzo[c]phenanthrene-2,2′-diols: HEBPOLs) 2a–b was conducted utilizing (1R)-(−)-menthyl chloroformate as a chiral resolving agent. Subsequent manipulation produced highly optically pure [>99% enantiomeric excess (ee)] quinone derivatives (P) and (M)-1a–b in very good yields. The absolute configuration of each product was confirmed based on circular dichroism (CD) spectra and X-ray crystal structure analysis.

Original language	English
Pages (from-to)	4491-4495
Number of pages	5
Journal	Tetrahedron Letters
Volume	58
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2017.10.027
Publication status	Published - Nov 29 2017
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2017.10.027

Cite this

@article{535f84b2a8bc458c90d3e00628bacad8,

title = "Diastereomeric process-based chiral resolution of helical quinone derivatives using (−)-menthyl chloroformate",

abstract = "Diastereomeric resolution of helically distorted polycondensed bisphenols (1,1′-bibenzo[c]phenanthrene-2,2′-diols: HEBPOLs) 2a–b was conducted utilizing (1R)-(−)-menthyl chloroformate as a chiral resolving agent. Subsequent manipulation produced highly optically pure [>99% enantiomeric excess (ee)] quinone derivatives (P) and (M)-1a–b in very good yields. The absolute configuration of each product was confirmed based on circular dichroism (CD) spectra and X-ray crystal structure analysis.",

author = "Mohammad Shahabuddin and Hossain, {Md Sharif} and Takao Kimura and Michinori Karikomi",

note = "Funding Information: We thank Ministry of Education, Culture, Sports, Science, and Technology (MEXT) of Japanese Government under (Monbukagakusho: MEXT) Scholarship and Creative Department for Innovation (CDI) for financial support. We are also grateful to Mr. Makoto Roppongi from the Advanced Instrumental Analysis Department of our university for technical support. Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

month = nov,

day = "29",

doi = "10.1016/j.tetlet.2017.10.027",

language = "English",

volume = "58",

pages = "4491--4495",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "48",

}

TY - JOUR

T1 - Diastereomeric process-based chiral resolution of helical quinone derivatives using (−)-menthyl chloroformate

AU - Shahabuddin, Mohammad

AU - Hossain, Md Sharif

AU - Kimura, Takao

AU - Karikomi, Michinori

N1 - Funding Information: We thank Ministry of Education, Culture, Sports, Science, and Technology (MEXT) of Japanese Government under (Monbukagakusho: MEXT) Scholarship and Creative Department for Innovation (CDI) for financial support. We are also grateful to Mr. Makoto Roppongi from the Advanced Instrumental Analysis Department of our university for technical support. Publisher Copyright: © 2017 Elsevier Ltd

PY - 2017/11/29

Y1 - 2017/11/29

N2 - Diastereomeric resolution of helically distorted polycondensed bisphenols (1,1′-bibenzo[c]phenanthrene-2,2′-diols: HEBPOLs) 2a–b was conducted utilizing (1R)-(−)-menthyl chloroformate as a chiral resolving agent. Subsequent manipulation produced highly optically pure [>99% enantiomeric excess (ee)] quinone derivatives (P) and (M)-1a–b in very good yields. The absolute configuration of each product was confirmed based on circular dichroism (CD) spectra and X-ray crystal structure analysis.

AB - Diastereomeric resolution of helically distorted polycondensed bisphenols (1,1′-bibenzo[c]phenanthrene-2,2′-diols: HEBPOLs) 2a–b was conducted utilizing (1R)-(−)-menthyl chloroformate as a chiral resolving agent. Subsequent manipulation produced highly optically pure [>99% enantiomeric excess (ee)] quinone derivatives (P) and (M)-1a–b in very good yields. The absolute configuration of each product was confirmed based on circular dichroism (CD) spectra and X-ray crystal structure analysis.

UR - http://www.scopus.com/inward/record.url?scp=85032679295&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85032679295&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2017.10.027

DO - 10.1016/j.tetlet.2017.10.027

M3 - Article

AN - SCOPUS:85032679295

VL - 58

SP - 4491

EP - 4495

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 48

ER -

Diastereomeric process-based chiral resolution of helical quinone derivatives using (−)-menthyl chloroformate

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this