Syntheses and reactions of silyl carbamates. 2. A new mode of cyclic carbamate formation from tert-butyldimethylsilyl carbamate
M Sakaitani, Y Ohfune
Index: Sakaitani, Masahiro; Ohfune, Yasufumi Journal of the American Chemical Society, 1990 , vol. 112, # 3 p. 1150 - 1158
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Citation Number: 71
Abstract
Abstract: Stereoselective construction of 1, 2 and 1, 3 amino hydroxyl systems was achieved by the intramolecular trapping of the N-tert-butyldimethylsilyloxycarbonyl species (silyl carbamate) activated by fluoride ion. The reaction of the silyl carbamate with 1, 2-syn mesylate 3 gave the 1, 2-anti cyclic carbamate 7, exclusively, with complete inversion of the original stereochemistry of the leaving group. On the other hand, AgF-or AgF/Pd (II)- ...
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