The major product formed in the following reaction sequence is
KHMDS removes an α-proton to give the potassium enolate, and an N-sulfonyloxaziridine (Davis reagent) transfers its oxygen to the enolate carbon, giving an α-hydroxy ketone after work-up.
The substrate is a 7,7-dimethylbicyclo[2.2.1]heptan-2-one. Only C-3 can enolise (C-1 is a bridgehead, so Bredt’s rule forbids an enolate there). The exo face of the C-2/C-3 enolate is shielded by the syn methyl group on the one-carbon bridge, so the bulky oxaziridine approaches from the endo face, as in the Davis hydroxylation of camphor. The new OH therefore occupies the endo position and the hydrogen at C-3 is exo.
A bridgehead hydroxy ketone would need enolisation towards the bridgehead, which is not possible. An amino ketone would require nitrogen transfer, whereas N-sulfonyloxaziridines transfer oxygen. The exo alcohol is the diastereomer formed by attack from the hindered face.
endo-3-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-2-one option is correct.
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Important Questions from Mixed Topic (MH-SET)
.................... is a client server application that identifies each host on the internet with a unique user-friendly name.
Every OS has a ................ or .......... which primarily resides in the main memory of the computer to perform some of the basic functions of the OS.
(i) Kernel
(ii) Interface
(iii) Nucleus
(iv) Compiler
Codes:
Which of the following are referred to as low level language?
(i) Machine language
(ii) Assembly language
(iii) High level language
(iv) Natural language
Codes:
Match the following:
List I List II (a) New York Public Library (i) Shelv AR (b) Miami University Augmented Research Group (ii) Smart library (c) Oula University Library (iii) Wolf Walk (d) North Carolina State University (iv) Find the future Codes:
Which part of the QR code represents the encoded data?
