Asymmetric epoxidation-ring

Catalytic Asymmetric Epoxide Ring-opening Chemistry... 

This chapter begins by classifying the combinations of oxidation/reduction processes with subsequent cationic transformations, though to date the details of only two examples have been published. The first example comprises an asymmetric epoxidation/ring expansion domino process of aryl-substituted cyclopropyl-idenes (e. g., 7-1) to provide chiral cyclobutanones 7-3 via 7-2, which was first described by Fukumoto and coworkers (Scheme 7.1) [2]. 

Scheme 7.1. Domino asymmetric epoxidation/ring expansion reaction.

Ready, J. M. Jacobsen, E. N. (2001) Highly active oligomeric (salen)Co catalysts for asymmetric epoxide ring opening Reaction, J. Am. Chem. Soc., 123 2687-2688. 

Wu, M. H. Jacobsen, E. N., An Efficient Formal Synthesis of Balanol via the Asymmetric Epoxide Ring Opening Reaction. Tetrahedron Lett. 1997, 38, 1693. 

Ready JM, Jacobsen EN (2002) A practical oligomeric [(salen)Co] catalyst for asymmetric epoxide ring-opening reactions. Angew Chem Int Ed 41 1374—1377... 

Catalytic asymmetric epoxide ring-opening chemistry 06M116. 

Hydrogenation catalyzed by palladium, platinum, or Raney nickel of 6 retains the stereogenic center of vicinal carbon, thus provides a complimentary access to chiral vicinal amino alcohols to the conventional routes such as asymmetric epoxide ring opening with amines and their related precursors. Employing lanthanum-(/ )-binaphthol complex to promote asymmetric nitroaldo reaction, followed by the reduction of nitro group, to form amino alcohols serves as the perfect example of this synthetic strategy. ... 

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