Authors: Zhu, H. J.; Jiang, J. X.; Ren, J.; Yan, Y. M.; Pittman Jr., C. U.

Source: Current Organic Synthesis, Volume 2, Number 4, October 2005 , pp. 547-587(41)

Publisher: Bentham Science Publishers

Abstract:

This review introduces the broad general topic of asymmetric organic synthetic reactions and reagents. Reagents containing both frequently used metallic ions, e.g. Zn++, Cu+(++) and Ru++, and rarely used ions, such as Ag+, employed in the construction of designed chiral centers, are updated here. Enantioselective 1,2-additions and 1,4-conjugate additions, transfer hydrogenations, and diasteroselective aldol reaction are discussed. The selectivities induced by chiral -, - or -chiral amino alcohols, chiral diols, chiral binaphthyl derivatives, chiral P,N-containing auxiliaries, and other ligands used to prepare chiral metallic complexes, were compared in each reaction system. The use of two or more metallic ions with a single chiral ligand has now become a more popular strategy to catalyze chiral-center-controlled processes. For example, only diethylzinc was used in enantioselective additions to aldehydes in early studies. Recently, the combination of Et2Zn and Cu++ in the selective additions has been used to achieve high ee% values and yields. Finally, quantum calculations have been used to obtain kinetic data to predict a reactions ee% values. For example, the calculated Gcal. values have a strong relationship with the obtained Gfit values which have the direct linkage with the ee% values.

Keywords: enantioselectivity; diastereoselectivity; conjugate addition; aldol reaction; hydrogenation; diels-alder

Document Type: Review article

DOI: http://dx.doi.org/10.2174/157017905774322677

Affiliations: 1: State Key Lab of Phyytochemistry and Plant Resources in West China, Kunming Institute of Botany, CAS.

Publication date: 2005-10-01

More about this publication?

• Current Organic Synthesis publishes in-depth reviews on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.

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