Aldoximes reactions with allylboronates

Treatment of synlanti mixtures of aldoximes (69) with allylboronates generates N-(homoallyl)hydrox-ylamines (70) in good yield (Scheme 6). - The anti oxime reacts faster than the syn isomer. N-(Ho-moallyl)hydroxylamines (70) have been converted to homoallylamines (71) (with iron(II) dihydrolipoate) and have been treated with aldehydes to generate highly functionalized nitrone intermediates (72) for use in 1,3-dipolar addition reactions. 

Allylboronates of type 103 react with equivalent amounts of aldoximes 102 (equation 73) giving allylhydroxylamines 104 in good yields. Similar reactions of aldoximes and glyoxylate oxime ethers with allyl bromide and indium also provide hydroxylamines. Additions of substituted allyl boronates to oximes produce mixtures of stereoisomers with ratio highly dependent on the steric size of substituents in both molecules. Addition of allyltri-n-butyltin to aldoxime ether 105 (equation 74) was found to proceed with a considerable diastereoselectivity. 

---

See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ ]

---