Synlett 2021; 32(16): 1625-1628
DOI: 10.1055/a-1328-0352
cluster
Modern Nickel-Catalyzed Reactions

Zn-Mediated Hydrodeoxygenation of Tertiary Alkyl Oxalates

Yang Ye
a   School of Materials Science and Engineering, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China
,
Guobin Ma
b   Center for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China
,
Ken Yao
a   School of Materials Science and Engineering, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China
b   Center for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China
,
Hegui Gong
a   School of Materials Science and Engineering, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China
b   Center for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China
› Author Affiliations
This work was supported by the National Natural Science Foundation of China (grants 21871173 and 21572140).


Abstract

Herein we describe a general, mild, and scalable method for hydrodeoxygenation of readily accessible tertiary alkyl oxalates by Zn/silane under Ni-catalyzed conditions. The reduction method is suitable for an array of structural motifs derived from tertiary alcohols that bear diverse functional groups, including the synthesis of a key intermediate en route to estrone.

Supporting Information



Publication History

Received: 29 October 2020

Accepted after revision: 02 December 2020

Accepted Manuscript online:
02 December 2020

Article published online:
07 January 2021

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