Stereochemistry of the reactions of substituted allylboronates with chiral aldehydes. Factors influencing aldehyde diastereofacial selectivity

WR Roush, MA Adam, AE Walts…

Index: Roush,W.R.; Adam,M.A.; Walts,A.E. Journal of the American Chemical Society, 1986 , vol. 108, p. 3422

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Citation Number: 167

Abstract

Abstract: The stereochemistry of the reactions of substituted allylboronates 5-9 with D- glyceraldehyde acetonide (4) and L-4-deoxythreose cyclohexyl ketal (2) is described. The reactions involving (Z)-crotylboronates 5 and 6 are exceptionally stereoselective, with selectivity for the major 3, 4-syn, 4, 5-anti adducts 19, 23, 27, and 31 approaching the limit defined by the isomeric purity of the reagents. The level of aldehyde diastereofacial ...

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