The Journal of Organic Chemistry

N, N'-Bis (2, 2, 2-trifluoroethyl)-N, N'-ethylenetartramide: An Improved Chiral Auxiliary for the Asymmetric Allylboration Reaction

WR Roush, PT Grover

Index: Roush, William R.; Grover, Paul T. Journal of Organic Chemistry, 1995 , vol. 60, # 12 p. 3806 - 3813

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Citation Number: 60

Abstract

In 1988, we reported the synthesis of allylboronate 4 containing a conformationally rigid tartramide auxiliary. 39 This reagent, designed on the basis of our rationale of the mechanism of asymmetric induction in allylboration reactions of 1-3, 24, 40 was found to be substantially more enantioselective than the parent tartrate ester derivative 1 (94-97% ee for most substrates except PhCH0). 39 The Banfi reagent 4 still ranks among the most highly ...

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