Catalytic asymmetric oxo-Diels-Alder reactions with chiral atropisomeric biphenyl diols

Chi Tung Yeung; Wesley Ting Kwok Chan; Wai Sum Lo; Ga Lai Law; Wing Tak Wong

doi:10.3762/bjoc.15.92

Catalytic asymmetric oxo-Diels-Alder reactions with chiral atropisomeric biphenyl diols

Chi Tung Yeung, Wesley Ting Kwok Chan, Wai Sum Lo, Ga Lai Law, Wing Tak Wong

Research output: Journal article publication › Journal article › Academic research › peer-review

Abstract

New chiral atropisomeric biphenyl diols 3, 4 and 6 containing additional peripheral chiral centers with different steric bulkiness and/or electronic properties were synthesized. The X-ray crystal structure of 3 shows the formation of a supramolecular structure whereas that of 6, containing additional CF₃ substituents, shows the formation of a monomeric structure. Diols 1-6 were found to be active organocatalysts in oxo-Diels-Alder reactions in which 2 recorded a 72% ee with trimethylacetaldehyde as a substrate.

Original language	English
Pages (from-to)	955-962
Number of pages	8
Journal	Beilstein Journal of Organic Chemistry
Volume	15
DOIs	https://doi.org/10.3762/bjoc.15.92
Publication status	Published - 2019

Keywords

Asymmetric organocatalysis
Axial chirality
Biaryls
Hydrogen bond
Oxo-Diels-Alder reaction

ASJC Scopus subject areas

Organic Chemistry

More information

10.3762/bjoc.15.92

http://hdl.handle.net/10397/81223

Cite this

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title = "Catalytic asymmetric oxo-Diels-Alder reactions with chiral atropisomeric biphenyl diols",

abstract = "New chiral atropisomeric biphenyl diols 3, 4 and 6 containing additional peripheral chiral centers with different steric bulkiness and/or electronic properties were synthesized. The X-ray crystal structure of 3 shows the formation of a supramolecular structure whereas that of 6, containing additional CF3 substituents, shows the formation of a monomeric structure. Diols 1-6 were found to be active organocatalysts in oxo-Diels-Alder reactions in which 2 recorded a 72% ee with trimethylacetaldehyde as a substrate.",

keywords = "Asymmetric organocatalysis, Axial chirality, Biaryls, Hydrogen bond, Oxo-Diels-Alder reaction",

author = "Yeung, {Chi Tung} and Chan, {Wesley Ting Kwok} and Lo, {Wai Sum} and Law, {Ga Lai} and Wong, {Wing Tak}",

note = "Funding Information: The authors gratefully acknowledge the fundings from the Basic Research Program of Shenzhen (No. JCYJ20160531184120814), State Key Laboratory of Chemical Biology and Drug Discovery, and The Hong Kong Polytechnic University [University Research Facility for Chemical and Environmental Analysis (UCEA)]. G.-L. Law gratefully acknowledges financial support from Natural Science Foundation of China (NSFC, 21875201) Publisher Copyright: {\textcopyright} 2019 Yeung et al.",

year = "2019",

doi = "10.3762/bjoc.15.92",

language = "English",

volume = "15",

pages = "955--962",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

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TY - JOUR

T1 - Catalytic asymmetric oxo-Diels-Alder reactions with chiral atropisomeric biphenyl diols

AU - Yeung, Chi Tung

AU - Chan, Wesley Ting Kwok

AU - Lo, Wai Sum

AU - Law, Ga Lai

AU - Wong, Wing Tak

N1 - Funding Information: The authors gratefully acknowledge the fundings from the Basic Research Program of Shenzhen (No. JCYJ20160531184120814), State Key Laboratory of Chemical Biology and Drug Discovery, and The Hong Kong Polytechnic University [University Research Facility for Chemical and Environmental Analysis (UCEA)]. G.-L. Law gratefully acknowledges financial support from Natural Science Foundation of China (NSFC, 21875201) Publisher Copyright: © 2019 Yeung et al.

PY - 2019

Y1 - 2019

N2 - New chiral atropisomeric biphenyl diols 3, 4 and 6 containing additional peripheral chiral centers with different steric bulkiness and/or electronic properties were synthesized. The X-ray crystal structure of 3 shows the formation of a supramolecular structure whereas that of 6, containing additional CF3 substituents, shows the formation of a monomeric structure. Diols 1-6 were found to be active organocatalysts in oxo-Diels-Alder reactions in which 2 recorded a 72% ee with trimethylacetaldehyde as a substrate.

AB - New chiral atropisomeric biphenyl diols 3, 4 and 6 containing additional peripheral chiral centers with different steric bulkiness and/or electronic properties were synthesized. The X-ray crystal structure of 3 shows the formation of a supramolecular structure whereas that of 6, containing additional CF3 substituents, shows the formation of a monomeric structure. Diols 1-6 were found to be active organocatalysts in oxo-Diels-Alder reactions in which 2 recorded a 72% ee with trimethylacetaldehyde as a substrate.

KW - Asymmetric organocatalysis

KW - Axial chirality

KW - Biaryls

KW - Hydrogen bond

KW - Oxo-Diels-Alder reaction

UR - http://www.scopus.com/inward/record.url?scp=85066476319&partnerID=8YFLogxK

U2 - 10.3762/bjoc.15.92

DO - 10.3762/bjoc.15.92

M3 - Journal article

AN - SCOPUS:85066476319

SN - 1860-5397

VL - 15

SP - 955

EP - 962

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Catalytic asymmetric oxo-Diels-Alder reactions with chiral atropisomeric biphenyl diols

Abstract

Keywords

ASJC Scopus subject areas

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