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Complete 1,3-asymmetric induction in the reactions of allenylboronic acid with β-hydroxy ketones

✍ Scribed by Nobuo Ikeda; Kenichi Omori; Hisashi Yamamoto


Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
200 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis


A novel reaction system is described for the complete stereoselective addition of carbanionic nucleophiles to ,+hydroxy ketones. Controlling l,n-asymmetric induction in nucleophilic addition to acyclic carbonyl compounds is one of the most powerful and useful synthetic methods in organic chemistry. Recently there has been extensive investigation in this area, and rather reliable methods now exist for achieving good stereoselectivity in additions to ff-and /3-alkoxy aldehydes. 1 Unfortunately,


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The reaction of a series of 4,4-dimethyl-3,5,5-(R3, R2, ## RI)-3-hydroxy-I,2-dioxolanes la-d [la (R, with trimethyl phosphite or triphenylphosphine produced the p-hydro.xy ketones, 2a-d [(R,R#70H)CMe2-COR3], and the corresponding phosphoryl compounds in high yield. The reactions were slow (-24 ho