A unified approach for divergent synthesis of contiguous stereodiads employing a small boronyl group

Miao Zhan, Zhengwei Ding, Shaozhi Du, Haohua Chen, Chao Feng, Ming Xu, Zhi Liu, Mengxi Zhang, Chao Wu, Yu Lan () and Pengfei Li ()
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Miao Zhan: Frontier Institute of Science and Technology, Xi’an Jiaotong University
Zhengwei Ding: Frontier Institute of Science and Technology, Xi’an Jiaotong University
Shaozhi Du: College of Chemistry & Pharmacy, Northwest A&F University
Haohua Chen: School of Chemistry and Chemical Engineering, and Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University
Chao Feng: Frontier Institute of Science and Technology, Xi’an Jiaotong University
Ming Xu: Frontier Institute of Science and Technology, Xi’an Jiaotong University
Zhi Liu: Frontier Institute of Science and Technology, Xi’an Jiaotong University
Mengxi Zhang: Frontier Institute of Science and Technology, Xi’an Jiaotong University
Chao Wu: Frontier Institute of Science and Technology, Xi’an Jiaotong University
Yu Lan: School of Chemistry and Chemical Engineering, and Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University
Pengfei Li: Frontier Institute of Science and Technology, Xi’an Jiaotong University

Nature Communications, 2020, vol. 11, issue 1, 1-9

Abstract: Abstract Acyclic contiguous stereocenters are frequently seen in biologically active natural and synthetic molecules. Although various synthetic methods have been reported, predictable and unified approaches to all possible stereoisomers are rare, particularly for those containing non-reactive hydrocarbon substituents. Herein, a β-boronyl group is employed as a readily accessible handle for predictable α-functionalization of enolates with either syn or anti selectivity depending on reaction conditions. Contiguous tertiary-tertiary and tertiary-quaternary stereocenters are thus accessed in generally good yields and diastereoselectivity. Based on experimental and computational studies, mechanism for syn selective alkylation is proposed, and Bpin (pinacolatoboronyl) behaves as a smaller group than most carbon-centered groups. The synthetic utility of this methodology is demonstrated by preparation of several key intermediates for bioactive molecules.

Date: 2020
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DOI: 10.1038/s41467-020-14592-7

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