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Felkin-Ahn transition state model

Murakami and Taguchi utilized a diastereoselective Grignard addition to a substituted-chiral oxazoline aldehyde 524 (Scheme 8.170) in an improved stereoselective synthesis of D-n7 o-phytosphingosine. The good stereoselectivity observed for 525 can be rationalized by a Felkin-Ahn transition state model although a chelation control mechanism could not be mled out. [Pg.477]

Fio. 4. Houk s transition state model (a) and the Felkin-Ahn transition state model (b) for the reaction of the dioxolane (48) with nitrile oxides. [Pg.281]

Stereoselective Carbonyl Reductions. L-selectride reduction of U-acyl-Y-lactones has been shown to furnish the syn-reduction products in good yield and high diastereoselection which may be hydrolysed to threo-diols. The stereochemistry appears to be largely independent of the size of the acyl group and is in accord with reduction following the Felkin-Ahn transition-state model (Scheme 2). ... [Pg.188]


See also in sourсe #XX -- [ Pg.477 ]




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