Asymmetric Synthesis of Biaryl Diols via Dynamic Kinetic Resolution

We have developed a protocol incuding dynamic kinetic resolution as the key step for the asymmetric synthesis of biaryl diol stereoisomers. The two aryl alkanols as the starting materials were cross‐coupled by palladium catalysis to give dl‐ and meso‐diol, which were then subject to chemoenzymatic d...

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Bibliographic Details
Published inBulletin of the Korean Chemical Society Vol. 42; no. 7; pp. 1028 - 1032
Main Authors Cho, Jeonghun, Kim, Kyungwoo, Park, Jaiwook, Kim, Mahn‐Joo
Format Journal Article
LanguageEnglish
Published Weinheim Wiley‐VCH Verlag GmbH & Co. KGaA 01.07.2021
대한화학회
Subjects
Asymmetric synthesis
Biaryl diols
Dynamic kinetic resolution
Lipase
Ruthenium catalyst
화학
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Summary:We have developed a protocol incuding dynamic kinetic resolution as the key step for the asymmetric synthesis of biaryl diol stereoisomers. The two aryl alkanols as the starting materials were cross‐coupled by palladium catalysis to give dl‐ and meso‐diol, which were then subject to chemoenzymatic dynamic kinetic resolution (DKR) for the transformation into single stereoisomeric diol diester. Diol diester was finally deacylated to give the corresponding biaryl diol stereoisomer. The chemoenzymatic DKR was performed with a ruthenium‐based racemization catalyst and a (R)‐selective lipoprotein lipase. Total 17 (R,R)‐diols including 7 C2‐symmetric diols were synthesized with excellent enantiopurities (>99% ee). We have developed a protocol for the asymmetric synthesis of biaryl diol stereoisomers. Our synthetic procedure employs lipase/ruthenium‐catalyzed DKR as the key step and provides (R,R)‐stereoisomers.
ISSN:1229-5949
0253-2964
1229-5949
DOI:10.1002/bkcs.12337