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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.

SUBMITTER: Yeung CT

PROVIDER: S-EPMC6541354 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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

Yeung Chi-Tung CT Chan Wesley Ting Kwok WTK Lo Wai-Sum WS Law Ga-Lai GL Wong Wing-Tak WT

Beilstein journal of organic chemistry 20190418

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 react ...[more]

PMID: 31164932

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