The Synthesis and Strecker Reaction of 2‑Chlorotetrafluoroethanesulfinyl Ketimines

A series of 2-chlorotetrafluoroethanesulfinyl
ketimines were prepared
from 2-chlorotetrafluoroethanesulfinamide and ketones in high yields,
and their Strecker reactions with TMSCN have been investigated. High
yields and excellent diastereoselectivities were achieved in the presence
of a catalytic amount of CsF under mild conditions. The six-membered
chairlike models were proposed to account for the high stereoselective
Strecker reaction.

本研究以2-氯四氟乙基亚磺酰胺（2-chlorotetrafluoroethanesulfinamide）与酮类为原料，以高产率合成了一系列2-氯四氟乙基亚磺酰基酮亚胺（2-chlorotetrafluoroethanesulfinyl ketimines），并对其与三甲基硅基氰（TMSCN）的斯特雷克反应（Strecker reaction）进行了考察。在温和反应条件下，采用催化量的氟化铯（CsF）作为催化剂时，该反应可获得优异的产率与极佳的非对映选择性。研究提出六元环椅式构象模型，用以阐释该高立体选择性斯特雷克反应的成因。