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Lewis base catalyzed asymmetric formal [2+2] cycloadditions

Smith, Andrew D., Douglas, James, Morrill, Louis C. and Richmond, Edward 2014. Lewis base catalyzed asymmetric formal [2+2] cycloadditions. In: Nishiwaki, Nagatoshi ed. Methods and Applications of Cycloaddition Reactions in Organic Syntheses, Wiley, pp. 89-114. (10.1002/9781118778173.ch03)

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Abstract

Research into the development of new catalytic modes, as exemplified by the rapidly expanding field of organocatalysis, has led to the efficient synthesis of polyfunctionalized molecules with routinely high levels of stereocontrol. This chapter focuses specifically on formal [2+2] cycloadditions catalyzed by Lewis bases, with an exclusive focus on those processes that have been rendered asymmetric. Detailed analysis of reaction design, mechanism, and product utility are made for a range of important four‐membered heterocyclic classes, beginning with β‐lactams and β‐lactones before further expanding to more elaborate architectures, such as aza‐β‐lactams, β‐sultams, and β‐sultones. It demonstrates the role and development of Lewis base catalysts in asymmetric ketene homodimerization, the potential utility of such stereodefined polyketide scaffolds, and the emerging field of asymmetric ketene heterodimerization.

Item Type: Book Section
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Wiley
ISBN: 9781118299883
Last Modified: 26 Feb 2019 10:04
URI: http://orca.cf.ac.uk/id/eprint/104800

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