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Chemistry. 2017 Jan 12;23(3):467-512. doi: 10.1002/chem.201602822. Epub 2016 Oct 10.

Gold-Catalyzed Enantioselective Annulations.

Li Y1, Li W1, Zhang J1,2.

Author information

1
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, P. R. China.
2
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032, China.

Abstract

In the past decade, there have been many extraordinary advances in the development of gold-catalyzed enantioselective annulations, such as cycloadditions, cyclizations, cycloisomerizations, and tandem annulations, which are of particular interest owing to their potential for rapid construction of optically active hetero- and carbocyclic molecules. This Review summarizes the methods to construct chiral cyclic compounds by gold-catalyzed enantioselective annulations reported since 2005. The Review is organized according to the general annulation types catalyzed by chiral gold complexes or chiral gold salts, which have four main types (cycloadditions, cyclizations of C-C multiple bonds with tethered nucleophiles, cycloisomerization or cyclization of enynes, and tandem annulations), as well as some other strategies. The general reaction mechanisms of each subcategory, key intermediates for some unusual transformations, and the application of several novel ligands and chiral gold salts are also discussed.

KEYWORDS:

annulation; cyclization; cycloaddition; enantioselectivity; gold

PMID:
27723131
DOI:
10.1002/chem.201602822

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