jo0c00851_si_001.pdf (2.73 MB)
Highly Diastereoselective Synthesis of 2,2-Disubstituted Cyclopentane-1,3-diols via Stepwise Ketone Reduction Enabling Concise Chirality Construction
journal contribution
posted on 2020-07-28, 22:29 authored by Jingyao Gong, Jianjiong Li, Xi Chen, Hongliu Zhang, Liangyan Zhu, Dandan Bu, Qin Wang, Jinhui Feng, Qiaqing Wu, Dunming ZhuA series
of 2,2-disubstituted trans,cis-cyclopentane-1,3-diols
were synthesized in >99% dr through enzymatic
reduction of enantiopure 2,2-disubstituted 3-hydroxycyclopentane-1-ones,
which were prepared by highly stereoselective enzymatic reduction
of the corresponding cyclodiketones. For 2-benzyl-2-methyl-3-oxocyclopentyl
acetate, acetylation of the hydroxyl group significantly affected
the reduction stereoselectivity, giving trans,cis-, trans,trans-, and cis,cis-2-benzyl-2-methyl-cyclopentane-1,3-diols
in stereomerically pure form. This efficient and environmentally friendly
method provides a practical approach to the synthesis of these chiral
building blocks in single stereoisomeric form, demonstrating the power
of biocatalysis in the concise chirality construction of complex chiral
molecules.