Literature DB >> 33356186

Diastereo- and Enantioselective Construction of Spirocycles by Nickel-Catalyzed Cascade Borrowing Hydrogen Cyclization.

Zhengtian Ding1, Yiming Wang1, Wenfeng Liu1, Yate Chen1, Wangqing Kong1.   

Abstract

Spirocycles play an important role in drug discovery and development owing to their inherent three-dimensionality and structural novelty. Despite the recent significant progress, the straightforward catalytic asymmetric assembly of spirocyclic scaffolds with multiple stereocenters from readily available starting materials remains a formidable challenge. Herein, we develop an unprecedented nickel-catalyzed one-pot synthesis of enantioenriched spiroindanones from easily available 1,6-enynes and o-formylarylboronic acids. The reaction proceeds smoothly under redox-neutral conditions, without the need for an additional hydrogen donor, and features a broad substrate scope and excellent regio-, enantio-, and diastereoselectivity.

Entities:  

Year:  2020        PMID: 33356186     DOI: 10.1021/jacs.0c10055

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  4 in total

1.  Rh(i)-catalyzed dimerization of ene-vinylidenecyclopropanes for the construction of spiro[4,5]decanes and mechanistic studies.

Authors:  Chao Ning; Kang-Hua Rui; Yin Wei; Min Shi
Journal:  Chem Sci       Date:  2022-06-01       Impact factor: 9.969

2.  Enantioselective Nickel-Catalyzed anti-Arylmetallative Cyclizations onto Acyclic Ketones.

Authors:  Harley Green; Stephen P Argent; Hon Wai Lam
Journal:  Chemistry       Date:  2021-03-05       Impact factor: 5.236

3.  Enantioselective difunctionalization of alkenes by a palladium-catalyzed Heck/borylation sequence.

Authors:  Yuanqi Wu; Lizuo Wu; Zhan-Ming Zhang; Bing Xu; Yu Liu; Junliang Zhang
Journal:  Chem Sci       Date:  2022-01-22       Impact factor: 9.825

Review 4.  Nickel-Catalyzed Arylative Cyclizations of Alkyne- and Allene-Tethered Electrophiles using Arylboron Reagents.

Authors:  Simone M Gillbard; Hon Wai Lam
Journal:  Chemistry       Date:  2022-01-27       Impact factor: 5.020

  4 in total

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