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Highly diastereoselective synthesis of α-trifluoromethylated α-propargylamines by acetylide addition to chiral CF3-substituted N-tert-butanesulfinyl ketimines by Hengqiao Xiao; Yangen Huang; Feng-Ling Qing is a Chemistry article available to read on EtoBox.

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A convenient and practical method for the preparation of enantiomerically pure a-trifluoromethylated apropargylamines is described. A range of enantiopure a-trifluoromethylated a-propargyl sulfinamides were obtained by the addition of lithium acetylides generated in situ with n-BuLi and terminal alkynes to diverse chiral CF 3 -substituted (S)-N-tert-butanesulfinyl ketimines in moderate to excellent yields (56-97%) and with uniformly excellent diastereoselectivities (>99:1) by using Ti(O i Pr) 4 as the catalyst and THF as the polar solvent. Enantiomerically pure a-trifluoromethylated a,a-dibranched propargyl amines were then readily obtained in excellent yields (87-97%) by acidic cleavage of the tert-butanesulfinyl group.

Who reads Highly diastereoselective synthesis of α-trifluoromethylated α-propargylamines by acetylide addition to chiral CF3-substituted N-tert-butanesulfinyl ketimines?

Author

Hengqiao Xiao; Yangen Huang; Feng-Ling Qing

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0957-4166)

Published

2010

Language

EN

Field

Chemistry (Physical Sciences)