- Intramolecular rearrangement of α-azidoperoxides: An efficient synthesis of tert-butyl esters
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An unprecedented intramolecular rearrangement of α-azidoperoxides, promoted by simple organic base to provide tert-butyl esters, has been presented. Further, a one-pot methodology consisting of in situ generation of the α-azidoperoxides from corresponding aldehydes followed by base-promoted rearrangement to obtain the desired ester has also been executed. Relevant mechanistic studies, to provide the proof for intramolecular alkoxy transfer, are investigated.
- Pramanik, Suman,Reddy, Reddy Rajasekhar,Ghorai, Prasanta
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p. 1393 - 1396
(2015/03/30)
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- Synthesis and asymmetric resolution of α-azido-peroxides
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An unprecedented synthesis of α-azido-peroxides has been developed using an FeCl3-catalyst starting from carbonyl, TMS-azide, and hydroperoxide. Further, a base promoted decomposition of synthesized secondary α-azido-peroxides to provide the corresponding tert-butyl esters has been disclosed. Finally, an asymmetric kinetic resolution of such α-azido-peroxides has also been developed to provide chiral α-azido-peroxides in excellent enantiopurity.
- Pramanik, Suman,Ghorai, Prasanta
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supporting information
p. 3832 - 3835
(2013/09/02)
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