Catalytic Methods in Asymmetric Synthesis : …
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At present only a few catalytic asymmetric C—C bond-forming reactions have been shown to be useful for constructing quaternary carbons, undoubtedly reflecting the additional steric challenge involved in forming all-carbon quaternary centers. This Perspective will examine the current state of such methods. The focus will be on reactions for which some generality has been documented, and several examples exist of reactions that proceed with enantiomeric selectivities of at least 9:1 [enantiomeric excesses (ees) >80%]. The discussion is organized by general reaction types that have proven useful, not by the more commonly used organizations that focus on one specific transformation or one family of asymmetric catalysts. It is hoped that this organization will highlight the many opportunities that exist for future discoveries in this area. The less general approach for forming all-carbon quaternary stereocenters in which a group-selective catalytic asymmetric reaction is used to desymmetrize a prochiral intermediate containing a quaternary carbon will be briefly mentioned also. No attempt to summarize this latter field will be made, as any catalytic asymmetric reaction could in principle be used in this approach. In four areas, catalytic methods for directly forming all-carbon stereocenters are most developed: Diels–Alder reactions, the combination of chiral carbon nucleophiles with carbon electrophiles, reactions of allylmetal intermediates with carbon nucleophiles, and intramolecular Heck reactions. Our discussion will begin with these reaction types.