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• W2044865665 abstract "The mechanistic foundations of the Lewis base catalyzed aldol addition reactions have been investigated. From a combination of low-temperature spectroscopic studies (29Si and 31P NMR) and kinetic analyses using a rapid-injection NMR apparatus (RINMR), a correlation of the ground states and transition structures for the aldolization reactions has been formulated. The aldol addition of the tert-butylsilyl ketene acetal of tert-butyl propanoate with 1-naphthaldehyde is efficiently catalyzed by a combination of silicon tetrachloride and chiral phosphoramide Lewis bases. The rates and selectivities of the aldol additions are highly dependent on the structure of the Lewis bases: bisphosphoramides give the highest rate and selectivity, whereas a related monophosphoramide reacts slowly and with low selectivity. The monophosphoramide shows no nonlinear behavior. All of the additions show a first-order kinetic dependence on silyl ketene acetal and 1-naphthaldehyde and a zeroth-order dependence on silicon tetrachloride. The kinetic order in catalyst is structure dependent and is either half-, two-thirds-, or first-order. All of the phosphoramides are saturated with silicon tetrachloride in some form, and the resting-state species are mixtures of monomeric and dimeric, pentacoordinate cationic, or hexacoordinate neutral complexes. These data allow the formulation of a unified mechanistic scheme based on the postulate of a common reactive intermediate for all catalysts." @default.
• W2044865665 created "2016-06-24" @default.
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• W2044865665 date "2009-07-31" @default.
• W2044865665 modified "2023-10-07" @default.
• W2044865665 title "On the Mechanism of Lewis Base Catalyzed Aldol Addition Reactions: Kinetic and Spectroscopic Investigations Using Rapid-Injection NMR" @default.
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• W2044865665 doi "https://doi.org/10.1021/ja902474j" @default.
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